BE659237A - - Google Patents
Info
- Publication number
- BE659237A BE659237A BE659237A BE659237A BE659237A BE 659237 A BE659237 A BE 659237A BE 659237 A BE659237 A BE 659237A BE 659237 A BE659237 A BE 659237A BE 659237 A BE659237 A BE 659237A
- Authority
- BE
- Belgium
- Prior art keywords
- hydroxy
- heated
- methyl
- diisobutoxy
- desc
- Prior art date
Links
- -1 dimethylmethoxymethylene Chemical group 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- 150000004702 methyl esters Chemical class 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- YULXLNIYDVZZSB-UHFFFAOYSA-N 1,2-bis(2-methylpropoxy)-4-nitrobenzene Chemical compound CC(C)COC1=CC=C([N+]([O-])=O)C=C1OCC(C)C YULXLNIYDVZZSB-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 208000003495 Coccidiosis Diseases 0.000 description 1
- 206010023076 Isosporiasis Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
- RHFZTBSULNJWEI-UHFFFAOYSA-N dimethyl 2-(methoxymethylidene)propanedioate Chemical compound COC=C(C(=O)OC)C(=O)OC RHFZTBSULNJWEI-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02M—SUPPLYING COMBUSTION ENGINES IN GENERAL WITH COMBUSTIBLE MIXTURES OR CONSTITUENTS THEREOF
- F02M45/00—Fuel-injection apparatus characterised by having a cyclic delivery of specific time/pressure or time/quantity relationship
- F02M45/02—Fuel-injection apparatus characterised by having a cyclic delivery of specific time/pressure or time/quantity relationship with each cyclic delivery being separated into two or more parts
- F02M45/04—Fuel-injection apparatus characterised by having a cyclic delivery of specific time/pressure or time/quantity relationship with each cyclic delivery being separated into two or more parts with a small initial part, e.g. initial part for partial load and initial and main part for full load
- F02M45/06—Pumps peculiar thereto
-
- A—HUMAN NECESSITIES
- A45—HAND OR TRAVELLING ARTICLES
- A45D—HAIRDRESSING OR SHAVING EQUIPMENT; EQUIPMENT FOR COSMETICS OR COSMETIC TREATMENTS, e.g. FOR MANICURING OR PEDICURING
- A45D40/00—Casings or accessories specially adapted for storing or handling solid or pasty toiletry or cosmetic substances, e.g. shaving soaps or lipsticks
- A45D40/26—Appliances specially adapted for applying pasty paint, e.g. using roller, using a ball
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02M—SUPPLYING COMBUSTION ENGINES IN GENERAL WITH COMBUSTIBLE MIXTURES OR CONSTITUENTS THEREOF
- F02M41/00—Fuel-injection apparatus with two or more injectors fed from a common pressure-source sequentially by means of a distributor
- F02M41/02—Fuel-injection apparatus with two or more injectors fed from a common pressure-source sequentially by means of a distributor the distributor being spaced from pumping elements
- F02M41/06—Fuel-injection apparatus with two or more injectors fed from a common pressure-source sequentially by means of a distributor the distributor being spaced from pumping elements the distributor rotating
- F02M41/063—Fuel-injection apparatus with two or more injectors fed from a common pressure-source sequentially by means of a distributor the distributor being spaced from pumping elements the distributor rotating the distributor and rotary valve controlling fuel passages to pumping elements being combined
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Combustion & Propulsion (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<Desc/Clms Page number 1>
Estera alkyliques inférieurs d'acides 6,7-di(alkoxy inférieur)-4- hydroxy-3-quinoléinecarboxyliques.
Le brevet principal n 640.906 concerne de nouveaux compo- ses chimiques, les esters alkyliques Inférieurs d'acide
5,7-di(alkoxy inférieur)-4-hydroxy-3-quinoléinecarboxyliques de ' formule:
EMI1.1
où R et R1 représentent des radicaux alkyles Inférieurs de 2 à 4 ¯ atomes de carbone et R2 représente un radical alkyle inférieur.
<Desc/Clms Page number 2>
La présente invention a pour objet des composés chimiques
EMI2.1
nouveaux correspondants la formule indiquée oï-dessuzo, dans ' laquelle R etR1 représentent chacun un radical diisobutyle
EMI2.2
et B2 repr4sénte ' un radical méthyle ou othyle.
Ces nouveaux composés, le 67-dxisbu,toxy-/-hydroxy..3- qu.nolé.neoarbo5ry.ate de méthyle ou d'éthyle, peuvent être obtenus suivant un ,des procédés décrits au brevet principal.
EMI2.3
De préférence (1) on réduit le 3,,-.d..sobutayn.trobenzène, (2) on met le produit de réduction obtenu sous (1) en contact ,¯.¯' avec un malonate de diméthylméthoxyméthylene ou de diéthylétho- xyméthylene (suivant le cas) en présence d'un agent de régulation thermique, et (3) on chauffe le mélange.
Ils se distinguent par une activité chimiothérapeutique élevée dans le traitement d'infections parasitaires chez les ani- maux, auxquels ils sont administrés en quantités de loin inférieu.. res aux doses toxiques dans la lutte contre la coccidiose. Une composition convenant à cet effet comprend 0,001 à environ 0,1% en poids délester méthylique ou éthylique de l'acide 6,7-
EMI2.4
diisobutoxy-4-hydroxy-3-quinoléinecarboxylique en mélange avec un véhicule comestible.
EXEMPLE 1 -
EMI2.5
¯ém7=Dii.sobu%oXY-±-hvdroxv-3-auinoléinecarboxYlate d'éthyle.
A une solution de 197 g (1,8 mole) de catéchol dans ' " 730 em3 d'éthanol on ajoute, sous atmosphère d'azote, 143 g (3,6 ' moles) d'hydroxyde de sodium en pastilles. Lorsque la formation du sel est achevée, on ajoute, goutte à goutte, entre 55 et 65 C.
EMI2.6
490 g (3,6 moles) de bromure deisobutyle. Le tube d'introduction d'azote est alors retiré et le mélange est chauffé au reflux pen- dant 17 heures. Le bromure de sodium est séparé par filtration et le filtrat est concentré.
Le résidu goudronneux est repris dans 2 litres d'eau et extrait à l'aide de 2 litres, puis à l'aide de 1 litre d'éther. Les extraits éthérés sont combinés et lavés deux.;
<Desc/Clms Page number 3>
fois avec 500 cm3 d'une solution d'hydroxyde de sodium à la%, puis deux fois avec 1 litre d'eau. Après séchage de la solution éthérée sur,du MgSO4, celle-ci est concentrée pour donner un résidu de 125 g (33%).
Tout en maintenant la température au-dessous de 25 C à l'aide d'un bain de glace, on ajoute, goutte à goutte, 105 g (0,47 mole) de 1,2=diisobutoxybenzène à une solution 1:1 d'eau et d'acide nitrique concentré. Après l'addition, le refroidissement est poursuivi jusqu'à ce que la réaction cesse d'être exother- mique. Le mélange est versé dans 2 litres d'eau glacée sous agita- tion. Le solide brun obtenu est filtré, lavé soigneusement avec de l'eau jusqu'à ce que les eaux de lavage ne soient plus acides, puis dissous dans du méthanol tiède et filtré. Une petite quantité d'eau est ajoutée pour provoques la cristallisation. Le produit re- cristallisé a un poids de 49 g (39%) et un point de fusion de 68 à 72 C.
A 2 g de Pd/C à 5% contenant 50% d'eau, on ajoute 16 g (0,06 mole) de 3,4-diisobutoxynitrobenzène et 200 cm3 d'étha- nol. La quantité théorique d'hydrogène est consommée après agita- tion pendant 20 minutes en atmosphère d'hydrogène. Le catalyseur est séparé par filtration et le filtrat est ajouté à 13 g (0,06 mo- le) de malonate de diéthyléthoxyméthylène et le mélange est chauffé au reflux en atmosphère d'azote pendant 1 heure.
Par refroidissement usqu'à la température ambiante, 18 g (74%) de oristaux blancs de l'anile se séparent, P.F.77-79 C Un échantillon de 56 g de l'anile préparé de cette façon est introduit dans 600 cm3 de "Dowtherm" et la solution est chauffée au reflux pendant 1 heure. Le produit solide est lavé avec de l'hexane pour donner 31 g (81%) de produit fondant à 282-284 C.
Deux recristallisations dans le diméthylformamide donnent 25 g du produit recherché ayant un point de fusion de 288-291 C.
<Desc/Clms Page number 4>
EMI4.1
<tb>
C <SEP> H <SEP> N
<tb>
EMI4.2
Calculé poUf '-20"27 N,15 666 7,53 3,8'i,
EMI4.3
<tb> Trouvé <SEP> 66,53 <SEP> 7,24 <SEP> 4,13
<tb>
EXEMPLE 2 -
EMI4.4
fi.. 7-Diisobutoxv-A-hvdroxv-3-aumoléme.carboxYlate de méthyle 1', fU-1158).
Aune solution de 3#4-dilsobutoxyanlline., on ajoute T 41 g de malonate de diméthylmêthoxyméthylène. La solution est chauffée au reflux pendant 2 heures et concentrée sous vide pour obtenir un résidu visqueux. Le résidu est chauffé au bain
EMI4.5
de vapeur et ajouté à 800 em3 de udowthermu bouillant.La solution est chauffée à l'ébullition pendant 20 minutes, puis'refroidie.
Le produit est filtré, lavé avec du puis avec de . l'acétone et séché. Le rendement en produit recherché brut est de 36 g (44%)' Une suspension du produit dans 250 cm3 de méthanol' est chauffée à l'ébullition pendant 5 minutes et filtrée à chaud pour donner 35 g de produit ayant un point de fusion de 278-281 C.
R E VE N D I C A T IONS.
Ester alkylique inférieur d'un acide 6,7-di(alkoxy
EMI4.6
inférieur)-4-hydroxy-3-QuiRolélneearboxylique suivant le brevet principal n 610.g06, de formule!
EMI4.7
dans laquelle R et R1 représentent chacun un radical diisobutyle et R2 représente un radical méthyle ou éthyle.
**ATTENTION** fin du champ DESC peut contenir debut de CLMS **.
<Desc / Clms Page number 1>
Lower alkyl estera of 6,7-di (lower alkoxy) -4-hydroxy-3-quinolinecarboxylic acids.
Principal Patent No. 640,906 relates to new chemicals, the Lower Alkyl Esters of Acid.
5,7-di (lower alkoxy) -4-hydroxy-3-quinolinecarboxylics of the formula:
EMI1.1
where R and R1 represent Lower alkyl radicals of 2 to 4 ¯ carbon atoms and R2 represents lower alkyl radical.
<Desc / Clms Page number 2>
The present invention relates to chemical compounds
EMI2.1
new correspondents the indicated formula oï-dessuzo, in which R andR1 each represent a diisobutyl radical
EMI2.2
and B2 represents a methyl or othyl radical.
These new compounds, methyl or ethyl 67-dxisbu, toxy - / - hydroxy..3- qu.nolé.neoarbo5ry.ate, can be obtained by one of the processes described in the main patent.
EMI2.3
Preferably (1) the 3 ,, -. D..sobutayn.trobenzene is reduced, (2) the reduction product obtained under (1) is brought into contact, ¯.¯ 'with a dimethylmethoxymethylene or diethylétho- malonate. xymethylene (as appropriate) in the presence of a heat regulating agent, and (3) the mixture is heated.
They are distinguished by high chemotherapeutic activity in the treatment of parasitic infections in animals, to which they are administered in quantities far below the toxic doses in the control of coccidiosis. A composition suitable for this purpose comprises 0.001 to about 0.1% by weight of the methyl or ethyl ester of 6,7- acid.
EMI2.4
diisobutoxy-4-hydroxy-3-quinolinecarboxylique mixed with an edible vehicle.
EXAMPLE 1 -
EMI2.5
¯em7 = Dii.sobu% oXY- ± -hvdroxv-3-auinolinecarboxYlate of ethyl.
To a solution of 197 g (1.8 mol) of catechol in 730 em3 of ethanol is added, under a nitrogen atmosphere, 143 g (3.6 moles) of sodium hydroxide in pellets. salt formation is complete, we add, drop by drop, between 55 and 65 C.
EMI2.6
490 g (3.6 moles) of deisobutyl bromide. The nitrogen introduction tube is then removed and the mixture is heated at reflux for 17 hours. The sodium bromide is separated by filtration and the filtrate is concentrated.
The tarry residue is taken up in 2 liters of water and extracted with 2 liters, then with 1 liter of ether. The ethereal extracts are combined and washed two .;
<Desc / Clms Page number 3>
times with 500 cm3 of sodium hydroxide solution at%, then twice with 1 liter of water. After drying the ethereal solution over MgSO4, it is concentrated to give a residue of 125 g (33%).
While maintaining the temperature below 25 C using an ice bath, 105 g (0.47 mol) of 1.2 = diisobutoxybenzene are added dropwise to a 1: 1 solution. water and concentrated nitric acid. After the addition, cooling is continued until the reaction ceases to be exothermic. The mixture is poured into 2 liters of ice-cold water with stirring. The brown solid obtained is filtered, washed thoroughly with water until the washings are no longer acidic, then dissolved in lukewarm methanol and filtered. A small amount of water is added to cause crystallization. The recrystallized product has a weight of 49 g (39%) and a melting point of 68-72 C.
To 2 g of 5% Pd / C containing 50% water, 16 g (0.06 mol) of 3,4-diisobutoxynitrobenzene and 200 cm3 of ethanol are added. The theoretical quantity of hydrogen is consumed after stirring for 20 minutes in a hydrogen atmosphere. The catalyst is filtered off and the filtrate is added to 13 g (0.06 mol) of diethylethoxymethylene malonate and the mixture is refluxed in a nitrogen atmosphere for 1 hour.
On cooling to room temperature 18 g (74%) of the white anile oristals separated, PF77-79 C. A 56 g sample of the anile prepared in this way was introduced into 600 cm3 of " Dowtherm "and the solution is heated at reflux for 1 hour. The solid product is washed with hexane to give 31 g (81%) of product melting at 282-284 C.
Two recrystallizations from dimethylformamide give 25 g of the desired product having a melting point of 288-291 C.
<Desc / Clms Page number 4>
EMI4.1
<tb>
C <SEP> H <SEP> N
<tb>
EMI4.2
Calculated for '-20 "27 N, 15 666 7.53 3.8'i,
EMI4.3
<tb> Found <SEP> 66.53 <SEP> 7.24 <SEP> 4.13
<tb>
EXAMPLE 2 -
EMI4.4
fi .. 7-Diisobutoxv-A-hvdroxv-3-aumoléme. 1 'methyl carboxylate, fU-1158).
41 g of dimethylmethoxymethylene malonate are added to a solution of 3 # 4-dilsobutoxyanlline. The solution is heated at reflux for 2 hours and concentrated in vacuo to obtain a viscous residue. The residue is heated in a bath
EMI4.5
of steam and added to 800 em3 of boiling udowthermu.The solution is heated to the boil for 20 minutes, then re-cooled.
The product is filtered, washed with then with de. acetone and dried. The yield of the desired crude product is 36 g (44%). A suspension of the product in 250 cm3 of methanol is heated to boiling for 5 minutes and filtered hot to give 35 g of product having a melting point of 278-281 C.
R E VE N D I C A T IONS.
Lower alkyl ester of a 6,7-di (alkoxy
EMI4.6
lower) -4-hydroxy-3-QuiRolélneearboxylique according to main patent No. 610.g06, of formula!
EMI4.7
in which R and R1 each represent a diisobutyl radical and R2 represents a methyl or ethyl radical.
** ATTENTION ** end of DESC field can contain start of CLMS **.
Claims (1)
Priority Applications (38)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB47650/63A GB1007590A (en) | 1962-04-09 | 1963-12-03 | Lower alkyl esters of 6,7-di(lower)alkoxy-4-hydroxy-3-quinolinecarboxylic acid |
| FR955807A FR1505313A (en) | 1962-04-09 | 1963-12-03 | Lower alkyl esters of 6, 7-dialkoxy (lower) -4-hydroxy-3-quinoline carboxylic acids and process for their preparation |
| FI2402/63A FI42719B (en) | 1962-04-09 | 1963-12-04 | |
| SE13524/63A SE309238B (en) | 1962-04-09 | 1963-12-05 | |
| DEN24124A DE1238476B (en) | 1962-04-09 | 1963-12-06 | Process for the preparation of lower alkyl esters of a 6,7-dialkoxy-4-hydroxy-3-quinolinecarboxylic acid which are suitable for combating parasitic infections in veterinary medicine |
| CH976467A CH464921A (en) | 1962-04-09 | 1963-12-06 | Process for the preparation of new lower alkyl esters of 6,7-di- (lower-alkoxy) -4-hydroxy-quinoline-3-carboxylic acids |
| NO63151151A NO119142B (en) | 1962-04-09 | 1963-12-06 | |
| CH1498263A CH449617A (en) | 1961-02-08 | 1963-12-06 | Process for the preparation of new lower alkyl esters of 6,7-di- (lower-alkoxy) -4-hydroxyquinoline-3-carboxylic acids |
| CH976367A CH464920A (en) | 1962-04-09 | 1963-12-06 | Process for the preparation of new lower alkyl esters of 6,7-di- (lower-alkoxy) -4-hydroxy-quinoline-3-carboxylic acids |
| BE640906A BE640906A (en) | 1962-04-09 | 1963-12-06 | |
| BR155240/63A BR6355240D0 (en) | 1962-04-09 | 1963-12-06 | PROCESS FOR THE PREPARATION OF LOWER ACID ESTERS 6 7-DI-ALCOXI- (LOWER) -4-HYDROXY-QUINOLINO-CARBOXYLIC |
| US380058A US3267106A (en) | 1962-04-09 | 1964-07-02 | Lower alkyl esters of 6, 7-di (lower) alkoxy-4-hydroxy-3-quinolinecarboxylic acid |
| SE592/65A SE323961B (en) | 1962-04-09 | 1965-01-16 | |
| US440621A US3290315A (en) | 1962-04-09 | 1965-03-17 | Esters of 6, 7-di (lower) alkoxy-4-hydroxy-3-quinolinecarboxylic acid |
| GB24400/65A GB1035179A (en) | 1962-04-09 | 1965-06-09 | Esters of 6,7-di-substituted-4-hydroxy-3-quinolinecarboxylic acid |
| NL6508117A NL6508117A (en) | 1962-04-09 | 1965-06-24 | |
| NL6508116A NL6508116A (en) | 1962-04-09 | 1965-06-24 | |
| FR22709A FR91254E (en) | 1962-04-09 | 1965-06-29 | 6,7-Dialkoxy (lower) -4-hydroxy-3-quinoline carboxylic acids, lower alkyl ester and process for their preparation |
| DK336165AA DK112657B (en) | 1962-04-09 | 1965-07-01 | Process for the preparation of antimicrobially active 6,7-diisobutoxy-4-hydroxy-3-quinolinecarboxylic acid esters. |
| CH919565A CH449618A (en) | 1961-02-08 | 1965-07-01 | Process for the preparation of new lower alkyl esters of 6,7-di- (lower alkoxy) -4-hydroxyquinoline-3-carboxylic acids |
| FR23220A FR1532232A (en) | 1962-04-09 | 1965-07-02 | Lower alkyl and lower alkenyl esters of 6, 7-dialkoxy and dialkenyloxy (lower) -4-hydroxy and acetoxy-3-quinoline carboxylic acids and process for their preparation |
| FI1583/65A FI44397B (en) | 1962-04-09 | 1965-07-02 | |
| IT14922/65A IT1051719B (en) | 1962-04-09 | 1965-07-02 | LOWER ALCHYL ESTERS |
| US486583A US3316147A (en) | 1962-04-09 | 1965-07-27 | Coccidial compositions containing lower alkyl esters of 6, 7-di(lower) alkoxy-4-hydroxy-3-quinolinecarboxylic acid |
| US486586A US3482985A (en) | 1962-04-09 | 1965-08-23 | Method of making animal food |
| BE670520A BE670520A (en) | 1962-04-09 | 1965-10-05 | |
| CH370466A CH467781A (en) | 1961-02-08 | 1966-03-15 | Process for the preparation of esters of 3-quinoline carboxylic acids |
| SE16906/67A SE330169B (en) | 1962-04-09 | 1966-03-15 | |
| NO162114A NO119178B (en) | 1962-04-09 | 1966-03-15 | |
| SE3399/66A SE343858B (en) | 1962-04-09 | 1966-03-15 | |
| DK134766AA DK114344B (en) | 1962-04-09 | 1966-03-16 | Process for the preparation of therapeutically active alkyl or allyl esters of 6,7-dialkoxy-3-quinolinecarboxylic acids. |
| DE19661620083 DE1620083A1 (en) | 1962-04-09 | 1966-03-16 | Process for the preparation of lower alkyl esters of 6,7-di-alkoxy-4-hydroxy-3-quinolinecarboxylic acid |
| NO16251066A NO121339B (en) | 1962-04-09 | 1966-04-06 | |
| CY37067A CY370A (en) | 1962-04-09 | 1967-02-23 | Esters of 6,7-di-substituted-4-hydroxy-3-quinolinecarboxylic acid |
| OA52814A OA114E (en) | 1962-04-09 | 1967-03-15 | |
| OA52813A OA02579A (en) | 1962-04-09 | 1967-03-15 | Lower alkyl esters of 6,7-dialkoxy (lower) -4-hydroxy-3-quinoleine carboxylic acids and process for their preparation. |
| NO16866067A NO121401B (en) | 1962-04-09 | 1967-06-20 | |
| MY196762A MY6700062A (en) | 1962-04-09 | 1967-12-31 | Ester of 6,7-di-substituted-4-hydroxy-3-quinolinecarboxylic acid |
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18580662A | 1962-04-09 | 1962-04-09 | |
| US24293362A | 1962-12-07 | 1962-12-07 | |
| US27285863A | 1963-04-15 | 1963-04-15 | |
| US380058A US3267106A (en) | 1962-04-09 | 1964-07-02 | Lower alkyl esters of 6, 7-di (lower) alkoxy-4-hydroxy-3-quinolinecarboxylic acid |
| BE8546 | 1965-02-03 | ||
| US440621A US3290315A (en) | 1962-04-09 | 1965-03-17 | Esters of 6, 7-di (lower) alkoxy-4-hydroxy-3-quinolinecarboxylic acid |
| US486583A US3316147A (en) | 1962-04-09 | 1965-07-27 | Coccidial compositions containing lower alkyl esters of 6, 7-di(lower) alkoxy-4-hydroxy-3-quinolinecarboxylic acid |
| US48658665A | 1965-08-23 | 1965-08-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE659237A true BE659237A (en) | 1965-08-03 |
Family
ID=27570140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE659237A BE659237A (en) | 1961-02-08 | 1965-02-03 |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE659237A (en) |
-
1965
- 1965-02-03 BE BE659237A patent/BE659237A/fr unknown
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