CS268590B1 - Method of 5-nitro-2-furan and 5-nitro-2-thiophene series' enamines preparation - Google Patents

Method of 5-nitro-2-furan and 5-nitro-2-thiophene series' enamines preparation Download PDF

Info

Publication number
CS268590B1
CS268590B1 CS88219A CS21988A CS268590B1 CS 268590 B1 CS268590 B1 CS 268590B1 CS 88219 A CS88219 A CS 88219A CS 21988 A CS21988 A CS 21988A CS 268590 B1 CS268590 B1 CS 268590B1
Authority
CS
Czechoslovakia
Prior art keywords
nitro
formula
acid
furan
dibromo
Prior art date
Application number
CS88219A
Other languages
Czech (cs)
Slovak (sk)
Other versions
CS21988A1 (en
Inventor
Daniel Ing Csc Vegh
Jaroslav Prof Ing Drsc Kovac
Original Assignee
Vegh Daniel
Kovac Jaroslav
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Vegh Daniel, Kovac Jaroslav filed Critical Vegh Daniel
Priority to CS88219A priority Critical patent/CS268590B1/en
Publication of CS21988A1 publication Critical patent/CS21988A1/en
Publication of CS268590B1 publication Critical patent/CS268590B1/en

Links

Landscapes

  • Furan Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Rleil sa nový sposob pripravy enaalnov 5-nltro-2-furánového a 5-nltro-2-tlofénového radu obecného vzorce I vyznačený týa, ie 3-/5-n1tro-2-furyl/propénové alebo 3-/5-n1tro-2-tIenyl/propénová kyselina vzorca II aa nechá reagovat s broaoa za vzniku 2,3-dlbróa-3-/5-n]tro-2-furyl/- proplónovej, rejp. 2,3-d1broa-3-/5-nltro- -2-t1enyl/proplonovej kyseliny vzorca III, ktoré připadne po IzolécH sa nechajú reagovat s prlslušnya sekundérnya aalnoa alebo prlairnya aalnoa v prostředí organických rozpůčlad!et.A new way of preparing enaalnes was looted 5-nitro-2-furan and 5-nitro-2-thiophene of formula (I) t, 3- (5-nitro-2-furyl) propenoic acid; 3- (5-nitro-2-phenyl) propenoic acid formula IIa and reacts with broaoa to form 2,3-dibromo-3- (5-n-trichloro-2-furyl) - proplonic, rejp. 2,3-d1broa-3/5-nltro- -2-tertienyl / proplonic acid of formula III which are recovered after Isolation react with prlslušnya sekundérnya aalnoa or prlairnya aalnoa in organic environment rozpůčlad! et.

Description

Vynález aa týk» spoaobu přípravy enanínov 5-nítro-2~furánového a 5-nitro-2-tiofénového radu obecného vzorca I ' o2nThe invention relates to a process for the preparation of enanines of the 5-nitro-2-furan and 5-nitro-2-thiophene series of the general formula I 'o 2 n

H-CH-NR R 1 2 (I) kde Z je O elebo 8 a NR R_ je N(CH„) .H-CH-NR R 1 2 (I) wherein Z is O or 8 and NR R 2 is N (CH 2).

z * n<chch3)2 z * n <chch 3 ) 2

N ¢2/ NH'N ¢ 2 / NH '

CH NH, »5CH NH, »5

CHgCH^H, (CH^CHNH, CH3O-ς^>-ΝΗ,CH 2 CH 2 H, (CH 2 CHNH, CH 3 O-η 2> - ΝΗ,

Enaminy májá široké uplatněni» v organické) syntéze /Cook A.G., Enamines, Synthesis, Structures and Reactions, Dekker, New York-London 1969/. Enaniny 5-nitro-2-furinoviho a 5-nitro-2-tiofénového radu vykazujá výrazná antibakteriálnu aktivitu a *ά predmetom intenzivneho výskumu /Végh D., Šejnkman A.K., Nivorožkin L.E., Kováč J., Dandárová M., Ivančo L.: Coll. Czech. Chem. Commun., £5, 155 /1980/; Végh D., Šejnkman A.K., Kovií J., Kondratenko G.P., Geonja N.I.: ZSSR A0 671 254/. Ich přípravy vychádzajá z vysoko reaktivnych 5-nitro-2-furyl- resp. 5-nitro-2-tíenylvínylhalogenídov reakciou s amínmi, konkrétné sekundárnými /Végh 0., Kováč J., Dandárová K.: Tetrahedron letters Jj, 969 /1980/; Végh D., Kováč J., Dandárová K., Ivančo L. Coll. Czech. Chem. Commun. 155 /1980//.Enamins are widely used in organic synthesis (Cook A.G., Enamines, Synthesis, Structures and Reactions, Dekker, New York-London 1969). The enanins of the 5-nitro-2-furin and 5-nitro-2-thiophene series show significant antibacterial activity and are the subject of intensive research / Végh D., Šejnkman AK, Nivorožkin LE, Kováč J., Dandárová M., Ivančo L .: Coll. Czech. Chem. Commun., £ 5, 155 (1980); Végh D., Šejnkman A.K., Kovií J., Kondratenko G.P., Geonja N.I .: USSR A0 671 254 /. Their preparations are based on highly reactive 5-nitro-2-furyl- resp. 5-nitro-2-thienylvinyl halides by reaction with amines, in particular secondary ones (Végh 0., Kováč J., Dandárová K .: Tetrahedron letters Jj, 969 (1980)); Végh D., Kováč J., Dandárová K., Ivančo L. Coll. Czech. Chem. Commun. 155/1980 //.

Uvedené nevýhody v podstatné) miere odstraňuje sposob podía vynálezu, ktorého podstata spočívá v tom, že 3-/5-nitro—2-furyl/propénová alebo 3-/5-nitro-2-tienyl/propénová kyselina vzorca II .These disadvantages are substantially eliminated by the process according to the invention, which consists in that 3- (5-nitro-2-furyl) propenoic acid or 3- (5-nitro-2-thienyl) propenoic acid of the formula II.

0 N—2--CH-CH-COOH (11) __________ 2 'zJ ______ ______ ____ kde Z znamená to isté ako vo vzorci I, sa nechá reagovat s brómom za vzniku 2,3-dibróm3/5-nitro-2-furyl/propiónove) alebo Z,3-dibróm-3-/5-nitro-2-tienyl/.propiónovej kyseliny vzorca 111 rr~λ í t t i 1 0 N-___/ '\_-CHBr-CHBr~COOH 'Z ' kde Z Je hoře uvedené, ktorá popřípadě po ízolácií sa nechá reagoval io sekundárným amínom zvoleným zo skupiny zahrnujáce) zláčeniny vzorce · 0 N — 2 - CH-CH-COOH ( 11 ) __________ 2 'of J ______ ______ ____ where Z is the same as in formula I, is reacted with bromine to give 2,3-dibromo / 5-nitro-2 furyl / propionic acid), or Z, 3-dibromo-3- / 5-nitro-2-thienyl / .propiónovej of formula 111 rr ~ tti λ s 1 0 N -___ / '\ _- CHBr CHBr-COOH ~' Z wherein Z is indicated above, which optionally, after isolation, is reacted with a secondary amine selected from the group consisting of compounds of the formula

ΗΝ(0Η3)2,ΗΝ(0Η23)2, Hn[cH(CH3)2]2» ' QnH * (2/41 '° O™ alebo s primárným amínom zvoleným zo skupiny zahrňujáce) zláčeniny vzorcaΗΝ (0Η 3) 2, ΗΝ (2 0Η 0Η 3) 2, H N [CH (CH3) 2] 2 » '* QNH (2/41" ™ ° H or a primary amine selected from the group zahrňujáce) zláčeniny formula

CH3NH2, CH3CH2NH2/ (CH3)2CHNH2, Q-NH2, CH30_-<^—’NH2' —'NH2# v prostředí organických rozpúJtadíel ako v kvapalných aromatických uhíovodíkoch ako....... v benzéne, toluéne, xyléne v éteroch ako v díetyléterí, tetrahydrofuráne, dfoxáne, 1,2-dímetoxyetáne, polyetylénglykole o strednej molekulové) hmotnosti 200 ai 600, ěalej v octane etylovom, acetonitrile, sirouhlíku, acetone a 2-butanóne alebo v ich zmesiach navzájem alebo s vodou pri teplotách 20 až 160 C.CH 3 NH 2 , CH 3 CH 2 NH 2 / (CH 3 ) 2 CHNH 2 , Q-NH 2 , CH 3 0 _- < ^ - ' NH 2' - ' NH 2 # in the environment of organic solvents as in liquid aromatic hydrocarbons as ....... in benzene, toluene, xylene in ethers as in diethyl ether, tetrahydrofuran, dfoxane, 1,2-dimethoxyethane, polyethylene glycol with an average molecular weight of 200 to 600, further in ethyl acetate, acetonitrile, carbon disulfide, acetone and 2-butanone or mixtures thereof with each other or with water at temperatures of 20 to 160 ° C.

CS 268 590 B1CS 268 590 B1

Reakcie prebiehajú podCa nasledujúcej schémy:The reactions proceed according to the following scheme:

H-CH-C00H + Br2 °2n —K /--CHBr-CHBr-COOH+HNR.R -4 'Z7 12H-CH-C00H + Br 2 ° 2 n —K /--CHBr-CHBr-COOH+HNR.R -4 'Z 7 12

O N—/^V-CH-CH-NR.R 1 2ON - N-CH-CH-NR.R 1 2

Látky podta vynálezu možno připravit aj posobenim málo bázických amtnov pK_ 6 ako BThe compounds of the invention can also be prepared by treating the low base amines pK_6 as B

Sú primárné aminy/ aromatické aminy.They are primary amines / aromatic amines.

Předmětný sposob využívá substituíno-fragmentaíné reakcie na rozdiel od doteraz používaných $NV reakcli. Nakotko substitúcie prebiehajú na nasýtenom uhlíku a predchádzajú fragmentaínú reakciu, májů širšie uplatneníe a představuji! nový typ reakcie.The present process utilizes substituent fragmentation reactions in contrast to the previously used $ N in the reaction. Since the substitutions take place on saturated carbon and precede the fragmentation reaction, they have a wider application and I present! new type of reaction.

Přiklad 1Example 1

19/3 g /0,1 mol/ 3-/5-nitro-2-furyl/propénovej kyseliny sa suspendovalo do 250 ml C$2 a pri teplote varu rozpúštadla v priebehu 3 h přidalo 16 g brómu. Po odfarbeni roztoku sa přidalo k intenzivně miešanému roztoku 30 g piperidínu a po 5 h miešania sa rozpúštadlo oddesti I ovalo za vákua. Získalo sa 17 g 1-/N-piperidyl/-2-/5-nitro-2-furyl/eténu ot.t. 77 až 79 °C.19/3 g (0.1 mol) of 3- (5-nitro-2-furyl) propenoic acid were suspended in 250 ml of C18 and 16 g of bromine were added at the boiling point of the solvent over a period of 3 hours. After decolorization of the solution, 30 g of piperidine were added to the vigorously stirred solution, and after stirring for 5 hours, the solvent was removed in vacuo. 17 g of 1- (N-piperidyl) -2- (5-nitro-2-furyl) ethene were obtained, m.p. 77-79 ° C.

Příklad 2Example 2

19/3 g /0,1 mol/ 3-/5-nitro-2-furylZpropénovej kyseliny v 300 ml dioxánu sa zmiešalo při teplote 40 C.s 216 g brómu a po 1 h zahrievania k varu rozpúštadla sa přidalo 30 g dímetylamínu naraz. Po 1 h miešania pri teplote laboratoria sa reakšná zmes zahrievala 2 h pri 100 až 110 °C. Po ochladení sa přefiltrovala cez 100 g sílíkagelu, eluent benzen-octan etylový. Získalo sa 17 g 1-N,N-d1metylamino-2-/5-nítro-2-furyl/etylénu o t.t. 65 až 67 °C.19/3 g (0.1 mol) of 3- (5-nitro-2-furyl) propenoic acid in 300 ml of dioxane were mixed at 40 DEG C. with 216 g of bromine and, after heating for 1 hour to the boiling point of the solvent, 30 g of dimethylamine were added all at once. After stirring at room temperature for 1 h, the reaction mixture was heated at 100-110 ° C for 2 h. After cooling, it was filtered through 100 g of silica gel, eluent benzene-ethyl acetate. 17 g of 1-N, N-dimethylamino-2- (5-nitro-2-furyl) ethylene of m.p. 65-67 ° C.

Přiklad 3Example 3

3,53 g 2,3-dibróm~3-/5~nitro-2-furyl/propiónovej kyseliny získanej halogenáciou 3-/5-nítro-2-furyl/propénovej kyseliny s bromom sa rozpustilo v 50 ml acetonitrilu a 50 ml acetonu a za intenzivneho miešania sa přidalo 4 g anizidínu. Po 3 h zahrievania na 60 až 70 °C sa zmes čistila filtráciou cez silikagel. Získalo sa 1,1 g 1-/4-aetoxyfenyl/am1no-2-/5-nitro-furyl/eténu o t.t. 123 až 127 °C.3.53 g of 2,3-dibromo-3- (5-nitro-2-furyl) propionic acid obtained by halogenation of 3- (5-nitro-2-furyl) propenoic acid with bromine were dissolved in 50 ml of acetonitrile and 50 ml of acetone and 4 g of anisidine were added with vigorous stirring. After heating at 60-70 ° C for 3 h, the mixture was purified by filtration through silica gel. 1.1 g of 1- (4-ethoxyphenyl) amino-2- (5-nitrofuryl) ethene of m.p. 123-127 ° C.

Přiklad 4Example 4

20,9 g /0,1 mot/ 3-/5-nitro-2-tienyl/propénovej kyseliny v 250 ml C$2 při teplote varu rozpúštadla sa zmiešalo s 16 g brómu. Po odfarbeni roztoku sa přidalo 14 g dimetylaminu a po 10 min miešania pri 20 °C sa zahrial do varu 1 h. Potom sa přidalo 50 ml polyetylénglykolu o strednej molekulové] hmotností 300 a sirouhlík sa oddest iloval. Teplota sa postupné zvýšila na 100 °C v priebehu 2 h. Po vyliati do vody sa získalo 11 g 1-N/N-dimetylamino-2-/5-nitro-2-tienyl/etánu o t.t. 126 až 127 °C.20.9 g / 0.1 mot / 3- / 5-nitro-2-thienyl / propenoic acid in 250 ml of C $ 2 at the boiling point of the solvent were mixed with 16 g of bromine. After decolorization of the solution, 14 g of dimethylamine were added and, after stirring for 10 minutes at 20 [deg.] C., the mixture was heated to reflux for 1 hour. Then 50 ml of polyethylene glycol with an average molecular weight of 300 were added and the carbon disulfide was distilled off. The temperature was gradually raised to 100 ° C over 2 h. After pouring into water, 11 g of 1-N (N-dimethylamino-2- (5-nitro-2-thienyl) ethane were obtained, m.p. 126-127 ° C.

Přiklad 5Example 5

20,9 g /0,1 mol/ 3-/5-nitro-2-tienyl/propénovej kyseliny a 16 g brómu sa zmiešalo v 100 ml 1,2-dimetoxyetánu a po 10 min miešania a zahrievania na 60 C sa přidalo naraz20.9 g (0.1 mol) of 3- (5-nitro-2-thienyl) propenoic acid and 16 g of bromine were mixed in 100 ml of 1,2-dimethoxyethane and, after stirring and heating at 60 DEG C. for 10 minutes, were added all at once.

CS 268 590 B1 g morfolinu v 200 ml acetonu. Po 3 h zahrievania do varu, vylůženA amóniovA so( sa odfiltrovala a filtrAt sa zahustil ku kryitali zAc i 1 . Získalo sa 12 g 1-N-morfol1no-2-/5-nitro-2-tienyl/etAnu o t.t. 167 až 168 °C.CS 268 590 B1 g of morpholine in 200 ml of acetone. After heating to reflux for 3 h, the ammonium salt was filtered off and the filter was concentrated to crystallize from Acc to give 12 g of 1-N-morpholino-2- (5-nitro-2-thienyl) ethane, mp 167-168. ° C.

Přiklad 6Example 6

35,3 g 2,3-d1bróm-3/5-nÍtro-2-fenyl/propionovej kyseliny ziskanej halogenAciou 3-/5-nitro-2-fenyl/propAnovej kyseliny s brómom sa rozpustilo v 500 ml benzAnu a za intenzivneho mieíania sa přidalo 0,22 mol aminu. Po 3 h zahrievania do varu finAlny produkt sa čistil filtrAciou cez silikagél. Získali sa anaminy vo výtažku 70 až 95 Xi35.3 g of 2,3-dibromo-3 (5-nitro-2-phenyl) propionic acid obtained by halogenation of 3- (5-nitro-2-phenyl) propanoic acid with bromine were dissolved in 500 ml of benzene and stirred vigorously with vigorous stirring. 0.22 mol of amine was added. After heating to reflux for 3 h, the final product was purified by filtration through silica gel. The anamines were obtained in a yield of 70 to 95 Xi

HN^Rg HN ^ Rg t.t. m.p. C) C) HN(ca3)2 HN (ca 3 ) 2 65 65 until 67 67 HN(CH2CH3)2 HN (CH 2 CH 3 ) 2 64 64 until 65 65 nh[ch(ch ) J nh [ch (ch) J 53 53 until 57 57 H<> H <> 129 129 until 130 130 hnO hnO 77 77 until 79 79 HnQ ' HnQ ' 86 86 until 88 88 HN^ ^NH r HN ^ ^ NH r 160 160 until 165 165 nh2ch3 nh 2 ch 3 fidevý olej oil oil

kovovofialový olej νμ2η 2°η3 nh2-ch(ch3)2 kovovoflalový olejmetal violet oil νμ 2 - ° η 2 ° η 3 nh 2 -ch (ch 3 ) 2 metal violet oil

ΝΗ2~~Ο^ ΝΗ 2 ~~ Ο ^ -och3 -och 3 123 až 127 123 to 127 NH2-O NH 2 -O 115 až 117 115 to 117 nh2—-θ-nh 2 —-θ- —CH 3 —CH 3 120 až 122 120 to 122 nh2—Onh 2 —O —Br —Br 137 až 140 137 to 140

, · A, · A

Látky podlá vynAlezu možno připravit sposobom uvedeným v přiklade 6 aj za použitia iných aromatických kvapalných uhtovodikov ako toluén, xylén resp. ich zmesi.The compounds according to the invention can also be prepared by the process described in Example 6 using aromatic liquid hydrocarbons other than toluene, xylene and mixtures thereof.

Claims (1)

PREDMET VYNÁLEZUOBJECT OF THE INVENTION 1. Sposob přípravy enaminov 5-nitro-2-furánovího a 5-nitro~2-tiofínovího radu obecního vzorca IProcess for the preparation of enamines of the 5-nitro-2-furan and 5-nitro-2-thiophine series of general formula I ON 2ON 2 HoCH-NR R 1 2 (I) kde Z Je o n(chch3)2, CH3 ch3ch2nh, alebo S a NR R Je N(CH ) , N(CH CH ) , 1 ~ »5 £ & &HoCH-NR R 1 2 (I) where Z is he (chch 3 ) 2 , CH 3 ch 3 ch 2 nh, or S and NR R is N (CH), N (CH CH), 1 ~ »5 £ && N^~\/ NCJ> ' nQ] ' N Cy NH' θ^ΝΗ, (CH ) CHNH, ON ^ ~ \ / N CJ>' n Q]' N Cy NH 'θ ^ ΝΗ, (CH) CHNH, O CH O 3CH O 3 vyznačený tým, že 3-Z5-nitro-2-íurylZpropínová alebo 3-Z5-nitro-2-tienylZpropénová kyselina vzorca IIcharacterized in that 3-Z5-nitro-2-furylpropionic acid or 3-Z5-nitro-2-thienylpropenoic acid of formula II 0 N—\ 7---CH-CH-COOH (II) 2 'z z kde Z znamení to istí ako vo vzorci I,sa nechá reagovat s bromom za vzniku 2,3-dibrom-3-/5-nitro-2-furylZpropiónovej, alebo 2z3-dibróat“3-/5-nitro-2-tienyl/prip1ónovej kyseliny vzorca IIIN- (7) CH-CH-COOH (II) 2 'z of which Z is the same as in formula I, is reacted with bromine to give 2,3-dibromo-3- [5-nitro- 2-furylpropionic acid, or 2 of 3-dibromo-3- (5-nitro-2-thienyl) propionic acid of formula III (III) kde Z Je to istí ako hoře uvedení, ktorí popřípadě po izolácii sa nechajů reagovat so sekundárným aminom zvoleným zo skupiny zahrnujúcej zlůčeniny vzorca(III) wherein Z is the same as above, which optionally, after isolation, is reacted with a secondary amine selected from the group consisting of compounds of formula HN(CH3)2/HN(CH2CH3)2f Ην{οΗ(ΟΗ3)2]2' hnQo,HN (CH 3 ) 2 / HN (CH 2 CH 3 ) 2f Ην {οΗ (ΟΗ 3 ) 2 ] 2 'hnQo, alebo s primárným aminom zvoleným zo skupiny zahrnujúcej zlůčeniny vzorcaor with a primary amine selected from the group consisting of compounds of formula CH3NH2, CH3CH2NH2, (CH3)2CHNH2, 3°~<Ο NH2' CH3“-·^—’NH2' Br-Z^V-í v prostřed! organických rozpúštadiel ako v kvapalných aromatických uhíovodikoch ako v benzíne, toluíne, xyline v íteroch ako v dietylíteri, tetrahydrofuráne, dioxáne, 1,2-dimetoxyetáne, polyetylinglykole o strednej molekulovej hmotnosti 200 až 600, ďalej v octane etylovom, acetonitrile, sirouhliku, acetone a 2-butanone alebo v ich zmesiach navzájom alebo s vodou pri teplotách 20 až 160 °C.CH 3 NH 2 , CH 3 CH 2 NH 2 , (CH 3 ) 2 CHNH 2 , 3 ° ~ <Ο NH 2 ' CH 3 “- · ^ -' NH 2 'Br-Z ^ V-í in the middle! organic solvents such as liquid aromatic hydrocarbons such as gasoline, toluine, xyline in ethers such as diethyl ether, tetrahydrofuran, dioxane, 1,2-dimethoxyethane, polyethylene glycol of an average molecular weight of 200 to 600, as well as ethyl acetate, acetonitrile, carbon monoxide and carbon disulphide 2-butanone or mixtures thereof with each other or with water at temperatures of 20 to 160 ° C.
CS88219A 1988-01-13 1988-01-13 Method of 5-nitro-2-furan and 5-nitro-2-thiophene series' enamines preparation CS268590B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CS88219A CS268590B1 (en) 1988-01-13 1988-01-13 Method of 5-nitro-2-furan and 5-nitro-2-thiophene series' enamines preparation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CS88219A CS268590B1 (en) 1988-01-13 1988-01-13 Method of 5-nitro-2-furan and 5-nitro-2-thiophene series' enamines preparation

Publications (2)

Publication Number Publication Date
CS21988A1 CS21988A1 (en) 1989-08-14
CS268590B1 true CS268590B1 (en) 1990-03-14

Family

ID=5333916

Family Applications (1)

Application Number Title Priority Date Filing Date
CS88219A CS268590B1 (en) 1988-01-13 1988-01-13 Method of 5-nitro-2-furan and 5-nitro-2-thiophene series' enamines preparation

Country Status (1)

Country Link
CS (1) CS268590B1 (en)

Also Published As

Publication number Publication date
CS21988A1 (en) 1989-08-14

Similar Documents

Publication Publication Date Title
Troutman et al. The synthesis of 2, 3-disubstituted-4-thiazolidones1
Snyder et al. 1-[5-Arylfurfurylidene) amino] hydantoins. A New Class of Muscle Relaxants
Sharma et al. Synthesis of novel tetrahydroimidazole derivatives and studies for their biological properties
JPS63243080A (en) Novel thiazole derivatives acting on the cholinergic system, production methods and pharmaceutical compositions
NL1010018C2 (en) Quinoline and quinazoline derivatives with corticotropin releasing factor (CRF) antagonistic effect.
RU2042663C1 (en) Benzene derivatives and their salts
RU2032680C1 (en) Method for production of benzhydryloxyethylpiperazine derivatives
CH521356A (en) Aromatic ethers
CH645887A5 (en) PIPERAZINE DERIVATIVES.
SU1387877A3 (en) Method of producing piperasine-containing derivatives of urea or thiourea,or their oxygen-addition salts
CS268590B1 (en) Method of 5-nitro-2-furan and 5-nitro-2-thiophene series&#39; enamines preparation
EP0093521A2 (en) Quinoline derivatives
CN110483425B (en) A kind of acylthiourea compound and its preparation method and the application of anti-influenza A virus
Andreani et al. Imidazo [2, 1‐b] thiazole carbamates and acylureas as potential insect control agents
Basavarajaiah et al. Synthesis and anti-microbial activity of (Z)-4-(4-substituted-thiazol-2-yl)-l-(2-oxoindolin-3-ylidene) semicarbazide and its derivatives
US4431664A (en) Compound with antiulcerogenic activity, process for the preparation thereof and pharmaceutical composition therefrom
US4581349A (en) Certain benzodiimidazoles and their use as radiation sensitizers
PL110639B1 (en) Method of producing new derivatives of 5,6-dihydro-3h-pyrimidinone-4
GB1604675A (en) Aminoalkylbenzenes
JPS60208949A (en) Novel diamine derivative, manufacture and medicine
EP0298703A1 (en) A thiophene derivative and process for preparing the same
FI86422B (en) FOERFARANDE FOER FRAMSTAELLNING AV N - / (2-IMIDAZOLIN-2-YL) METHYL / -2-HYDROXI-4-AMINO-5-HALOGENBENAMIDER, VILKA AER ANVAENDBARA SAOSOM GASTROMOTORISKA CEEKEMEDEL.
EP0078757B1 (en) Imines of 2-(4-phenyl-piperazinylethyl) anilines, process for their preparation and their use in medicine
JPH033674B2 (en)
RU2690184C1 (en) Method of producing n-(4-sulphamoylphenyl)benzamidine