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)
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 (fr) | 1962-04-09 | 1963-12-03 | Esters d'alkyle inférieur des acides 6, 7-dialkoxy (inférieur)-4-hydroxy-3-quinoléine carboxyliques et leur procédé de préparation |
| FI2402/63A FI42719B (d) | 1962-04-09 | 1963-12-04 | |
| SE13524/63A SE309238B (d) | 1962-04-09 | 1963-12-05 | |
| NO63151151A NO119142B (d) | 1962-04-09 | 1963-12-06 | |
| DEN24124A DE1238476B (de) | 1962-04-09 | 1963-12-06 | Verfahren zur Herstellung von zur Bekaempfung von parasitaeren Infektionen in der Tiermedizin geeigneten niedrigeren Alkylestern einer 6, 7-Dialkoxy-4-hydroxy-3-chinolincarbonsaeure |
| CH1498263A CH449617A (de) | 1961-02-08 | 1963-12-06 | Verfahren zur Herstellung von neuen niederen Alkylestern von 6,7-Di-(niederalkoxy)-4-hydroxychinolin-3-carbonsäuren |
| BR155240/63A BR6355240D0 (pt) | 1962-04-09 | 1963-12-06 | Processo para preparacao de esteres inferiores de acido 6 7-di-alcoxi-(inferior)-4-hidroxi-quinolino-carboxilico |
| CH976467A CH464921A (de) | 1962-04-09 | 1963-12-06 | Verfahren zur Herstellung von neuen niederen Alkylestern von 6,7-Di-(niederalkoxy)-4-hydroxy-chinolin-3-carbonsäuren |
| BE640906A BE640906A (d) | 1962-04-09 | 1963-12-06 | |
| CH976367A CH464920A (de) | 1962-04-09 | 1963-12-06 | Verfahren zur Herstellung von neuen niederen Alkylestern von 6,7-Di-(niederalkoxy)-4-hydroxy-chinolin-3-carbonsäuren |
| 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 (d) | 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 |
| NL6508116A NL6508116A (d) | 1962-04-09 | 1965-06-24 | |
| NL6508117A NL6508117A (d) | 1962-04-09 | 1965-06-24 | |
| FR22709A FR91254E (fr) | 1962-04-09 | 1965-06-29 | Ester d'alkyle inférieur des acides 6, 7-dialkoxy (inférieur)-4-hydroxy-3-quinoléine carboxyliques et leur procédé de préparation |
| CH919565A CH449618A (de) | 1961-02-08 | 1965-07-01 | Verfahren zur Herstellung von neuen niederen Alkylestern von 6,7-Di-(nieder alkoxy)-4-hydroxychinolin-3-carbonsäuren |
| DK336165AA DK112657B (da) | 1962-04-09 | 1965-07-01 | Fremgangsmåde til fremstilling af antimikrobielt virksomme 6,7-diisobutoxy-4-hydroxy-3-kinolinkarboxylsyreestere. |
| IT14922/65A IT1051719B (it) | 1962-04-09 | 1965-07-02 | Esteri alchilici inferiori |
| FR23220A FR1532232A (fr) | 1962-04-09 | 1965-07-02 | Esters d'alkyle et d'alkényle inférieur des acides 6, 7-dialkoxy et dialkényloxy (inférieur)-4-hydroxy et acétoxy-3-quinoléine carboxyliques et leur procédé de préparation |
| FI1583/65A FI44397B (d) | 1962-04-09 | 1965-07-02 | |
| 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 (d) | 1962-04-09 | 1965-10-05 | |
| CH370466A CH467781A (de) | 1961-02-08 | 1966-03-15 | Verfahren zur Herstellung von Estern von 3-Chinolincarbonsäuren |
| SE3399/66A SE343858B (d) | 1962-04-09 | 1966-03-15 | |
| SE16906/67A SE330169B (d) | 1962-04-09 | 1966-03-15 | |
| NO162114A NO119178B (d) | 1962-04-09 | 1966-03-15 | |
| DK134766AA DK114344B (da) | 1962-04-09 | 1966-03-16 | Fremgangsmåde til fremstilling af terapeutisk aktive alkyl- eller allylestere af 6,7-dialkoxy-3-kinolinkarboxylsyrer. |
| DE19661620083 DE1620083A1 (de) | 1962-04-09 | 1966-03-16 | Verfahren zur Herstellung von niederen Alkylestern der 6,7-di-Alkoxy-4-hydroxy-3-chinolincarbonsaeure |
| NO16251066A NO121339B (d) | 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 |
| OA52813A OA02579A (fr) | 1962-04-09 | 1967-03-15 | Esters d'alkyle inférieur des acides 6,7-dialkoxy (inférieur)-4-hydroxy-3-quinoleine carboxyliques et leur procédé de préparation. |
| OA52814A OA114E (d) | 1962-04-09 | 1967-03-15 | |
| NO16866067A NO121401B (d) | 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 (d) | 1965-08-03 |
Family
ID=27570140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE659237A BE659237A (d) | 1961-02-08 | 1965-02-03 |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE659237A (d) |
-
1965
- 1965-02-03 BE BE659237A patent/BE659237A/fr unknown
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