DD268687A5 - Verfahren zur herstellung von kondensationsprodukten von 2,2,4-trimethyl-1,2-dihydrochinolin mit oxoverbindungen und deren derivaten - Google Patents

Verfahren zur herstellung von kondensationsprodukten von 2,2,4-trimethyl-1,2-dihydrochinolin mit oxoverbindungen und deren derivaten Download PDF

Info

Publication number: DD268687A5
Authority: DD; German Democratic Republic
Prior art keywords: trimethyl; product; dihydroquinoline; condensation products; parts
Prior art date: 1987-04-22

Application number

DD88315005A

Other languages

German (de)

English (en)

Inventor

Janos Szvoboda

Tamas Rozsnyai

Jozsef Szente

Laszlo Melovits

Imre Oetvoes

Ilona Legradi

Laszlo Prohaszka

Jenoe Fekete

Original Assignee

Material Vegyipari Kisszoevetkezet,Hu

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.)

1987-04-22

Filing date

1988-04-22

Publication date

1989-06-07

1988-04-22 Application filed by Material Vegyipari Kisszoevetkezet,Hu filed Critical Material Vegyipari Kisszoevetkezet,Hu

1989-06-07 Publication of DD268687A5 publication Critical patent/DD268687A5/de

Links

239000007859 condensation product Substances 0.000 title claims abstract description 6
ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 title abstract description 15
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 27
238000000034 method Methods 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
229910001420 alkaline earth metal ion Inorganic materials 0.000 claims abstract description 4
238000002360 preparation method Methods 0.000 claims abstract description 4
230000008569 process Effects 0.000 claims abstract description 4
239000003513 alkali Substances 0.000 claims abstract description 3
239000003963 antioxidant agent Substances 0.000 abstract description 21
150000003839 salts Chemical class 0.000 abstract description 12
239000002253 acid Substances 0.000 abstract description 11
239000002585 base Substances 0.000 abstract description 7
150000002576 ketones Chemical class 0.000 abstract description 7
125000002252 acyl group Chemical group 0.000 abstract description 4
230000002192 coccidiostatic effect Effects 0.000 abstract description 4
239000003054 catalyst Substances 0.000 abstract description 3
239000003426 co-catalyst Substances 0.000 abstract description 3
239000002904 solvent Substances 0.000 abstract description 3
229910001413 alkali metal ion Inorganic materials 0.000 abstract description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
239000000047 product Substances 0.000 description 28
235000006708 antioxidants Nutrition 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
230000003078 antioxidant effect Effects 0.000 description 14
239000000203 mixture Substances 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
229960001413 acetanilide Drugs 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
239000011734 sodium Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
KQXDHUJYNAXLNZ-XQSDOZFQSA-N Salinomycin Chemical compound O1[C@@H]([C@@H](CC)C(O)=O)CC[C@H](C)[C@@H]1[C@@H](C)[C@H](O)[C@H](C)C(=O)[C@H](CC)[C@@H]1[C@@H](C)C[C@@H](C)[C@@]2(C=C[C@@H](O)[C@@]3(O[C@@](C)(CC3)[C@@H]3O[C@@H](C)[C@@](O)(CC)CC3)O2)O1 KQXDHUJYNAXLNZ-XQSDOZFQSA-N 0.000 description 5
239000004189 Salinomycin Substances 0.000 description 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
230000008018 melting Effects 0.000 description 5
238000002844 melting Methods 0.000 description 5
210000003250 oocyst Anatomy 0.000 description 5
239000001294 propane Substances 0.000 description 5
229960001548 salinomycin Drugs 0.000 description 5
235000019378 salinomycin Nutrition 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
239000003224 coccidiostatic agent Substances 0.000 description 4
238000002845 discoloration Methods 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
235000013305 food Nutrition 0.000 description 4
239000000463 material Substances 0.000 description 4
238000002560 therapeutic procedure Methods 0.000 description 4
ADHZMOYUJKFKSE-UHFFFAOYSA-N 2,2,4-trimethyl-6-[(2,2,4-trimethyl-1h-quinolin-6-yl)methyl]-1h-quinoline Chemical compound N1C(C)(C)C=C(C)C2=CC(CC3=CC=C4NC(C)(C)C=C(C4=C3)C)=CC=C21 ADHZMOYUJKFKSE-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
229930191564 Monensin Natural products 0.000 description 3
GAOZTHIDHYLHMS-UHFFFAOYSA-N Monensin A Natural products O1C(CC)(C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CCC1C(O1)(C)CCC21CC(O)C(C)C(C(C)C(OC)C(C)C(O)=O)O2 GAOZTHIDHYLHMS-UHFFFAOYSA-N 0.000 description 3
-1 N-propyl Chemical group 0.000 description 3
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 description 3
PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
229960005358 monensin Drugs 0.000 description 3
GAOZTHIDHYLHMS-KEOBGNEYSA-N monensin A Chemical compound C([C@@](O1)(C)[C@H]2CC[C@@](O2)(CC)[C@H]2[C@H](C[C@@H](O2)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CO)O2)C)C)C[C@@]21C[C@H](O)[C@@H](C)[C@@H]([C@@H](C)[C@@H](OC)[C@H](C)C(O)=O)O2 GAOZTHIDHYLHMS-KEOBGNEYSA-N 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 3
IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical class C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 description 2
VFXMBRDLBJICQZ-UHFFFAOYSA-N 2,2,4-trimethyl-6-[1-(2,2,4-trimethyl-1h-quinolin-6-yl)ethyl]-1h-quinoline Chemical compound N1C(C)(C)C=C(C)C2=CC(C(C=3C=C4C(C)=CC(C)(C)NC4=CC=3)C)=CC=C21 VFXMBRDLBJICQZ-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
230000003712 anti-aging effect Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000001273 butane Substances 0.000 description 2
125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 description 2
DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
230000006641 stabilisation Effects 0.000 description 2
238000011105 stabilization Methods 0.000 description 2
238000006277 sulfonation reaction Methods 0.000 description 2
HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical class CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
239000005749 Copper compound Substances 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
239000002211 L-ascorbic acid Substances 0.000 description 1
235000000069 L-ascorbic acid Nutrition 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
208000019155 Radiation injury Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
210000000577 adipose tissue Anatomy 0.000 description 1
230000032683 aging Effects 0.000 description 1
150000001340 alkali metals Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910001424 calcium ion Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000008859 change Effects 0.000 description 1
150000001880 copper compounds Chemical class 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000003651 drinking water Substances 0.000 description 1
235000020188 drinking water Nutrition 0.000 description 1
JROGBPMEKVAPEH-GXGBFOEMSA-N emetine dihydrochloride Chemical compound Cl.Cl.N1CCC2=CC(OC)=C(OC)C=C2[C@H]1C[C@H]1C[C@H]2C3=CC(OC)=C(OC)C=C3CCN2C[C@@H]1CC JROGBPMEKVAPEH-GXGBFOEMSA-N 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
208000005053 encephalomalacia Diseases 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
GFAUNYMRSKVDJL-UHFFFAOYSA-N formyl chloride Chemical compound ClC=O GFAUNYMRSKVDJL-UHFFFAOYSA-N 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
KJNFMGMNZKFGIE-UHFFFAOYSA-N n-(4-hydroxyphenyl)acetamide;5-(2-methylpropyl)-5-prop-2-enyl-1,3-diazinane-2,4,6-trione;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)NC1=CC=C(O)C=C1.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.CC(C)CC1(CC=C)C(=O)NC(=O)NC1=O KJNFMGMNZKFGIE-UHFFFAOYSA-N 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
230000035764 nutrition Effects 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
244000144977 poultry Species 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
238000010998 test method Methods 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1

Classifications

- 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
- C07D215/04—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/08—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms with acylated ring nitrogen atom
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/137—Heterocyclic compounds containing two hetero atoms, of which at least one is nitrogen
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K30/00—Processes specially adapted for preservation of materials in order to produce animal feeding-stuffs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- 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
- C07D215/04—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
- 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
- C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member

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Chemical & Material Sciences (AREA)
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Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Compositions Of Macromolecular Compounds (AREA)

DD88315005A 1987-04-22 1988-04-22 Verfahren zur herstellung von kondensationsprodukten von 2,2,4-trimethyl-1,2-dihydrochinolin mit oxoverbindungen und deren derivaten DD268687A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU871740A HU200165B (en)	1987-04-22	1987-04-22	Process for producing dihydroquinoline derivatives, as well as pharmaceutical compositions, fodders and fodder premixes comprising such compounds

Publications (1)

Publication Number	Publication Date
DD268687A5 true DD268687A5 (de)	1989-06-07

Family

ID=10955955

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88315005A DD268687A5 (de)	1987-04-22	1988-04-22	Verfahren zur herstellung von kondensationsprodukten von 2,2,4-trimethyl-1,2-dihydrochinolin mit oxoverbindungen und deren derivaten

Country Status (7)

Country	Link
US (1)	US4994469A (fr)
EP (1)	EP0310648B1 (fr)
AU (1)	AU1627088A (fr)
CA (1)	CA1329602C (fr)
DD (1)	DD268687A5 (fr)
HU (1)	HU200165B (fr)
WO (1)	WO1988008420A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5202338A (en) *	1990-10-31	1993-04-13	Vilmos Bar	Dihydroquinoline derivatives, pharmaceutical compositions and methods of use of dihydroquinoline derivatives as modulators of the arachidonic acid cascade
EP0497735A1 (fr) *	1991-01-31	1992-08-05	Ciba-Geigy Ag	Composés d'hydroquinoléine
DE10329860A1 (de) *	2003-07-02	2005-01-20	Atto-Tec Gmbh	Sulfonamidderivate polycyclischer Farbstoffe für analytische Anwendungen

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE788509A (fr) *	1971-09-07	1973-01-02	Material Vegyi	Derives de dihydroquinoleine et procede de preparation
US4046765A (en) *	1971-09-07	1977-09-06	Material Ksz.	Dihydroquinoline derivatives of antioxidant activity and a process for the preparation thereof
HU185208B (en) *	1979-07-06	1984-12-28	Material Vegyipari Sz	Process for producing the water-soluble derivatives of 6,6-methylene-bis/2,2,4-trimetyl-1,2-dihidric quinoline/
US4510147A (en) *	1979-07-06	1985-04-09	Material Vegyipari Szovetkezet	Compositions for and medical use of water-soluble derivatives of 6,6-methylene-bis-(2,2,4-trimethyl-1,2-dihydroquinoline)
HU191576B (en) *	1984-11-13	1987-03-30	Bcr Muevek	Method for producing food having improved anticoccidiosis effect

1987
- 1987-04-22 US US07/301,887 patent/US4994469A/en not_active Expired - Fee Related
- 1987-04-22 HU HU871740A patent/HU200165B/hu not_active IP Right Cessation
1988
- 1988-04-21 CA CA000564661A patent/CA1329602C/fr not_active Expired - Fee Related
- 1988-04-22 AU AU16270/88A patent/AU1627088A/en not_active Abandoned
- 1988-04-22 EP EP88903342A patent/EP0310648B1/fr not_active Expired - Lifetime
- 1988-04-22 DD DD88315005A patent/DD268687A5/de not_active IP Right Cessation
- 1988-04-22 WO PCT/HU1988/000026 patent/WO1988008420A1/fr not_active Ceased

Also Published As

Publication number	Publication date
CA1329602C (fr)	1994-05-17
EP0310648B1 (fr)	1992-12-23
US4994469A (en)	1991-02-19
EP0310648A1 (fr)	1989-04-12
HU200165B (en)	1990-04-28
WO1988008420A1 (fr)	1988-11-03
AU1627088A (en)	1988-12-02

Legal Events

Date	Code	Title
1994-06-23	RPI	Change in the person, name or address of the patentee (searches according to art. 11 and 12 extension act)
1994-06-23	RPV	Change in the person, the name or the address of the representative (searches according to art. 11 and 12 extension act)
1999-01-07	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
CH395136A (de)	1965-07-15	Verfahren zur Herstellung von Xanthenen oder Thiaxanthenen
EP0039844A2 (fr)	1981-11-18	Procédé de préparation de dérivés O-substitués de (+)-cyanidan-3-ols
DD201903A5 (de)	1983-08-17	Verfahren zur herstellung von derivaten des thienopyridonons
DD268687A5 (de)	1989-06-07	Verfahren zur herstellung von kondensationsprodukten von 2,2,4-trimethyl-1,2-dihydrochinolin mit oxoverbindungen und deren derivaten
DE1933112C3 (de)	1975-05-15	Substituierte 1,3-Bis-(benzylidenamino)-guanidine
DE2322486C2 (de)	1982-06-03	as-Triazino [5,6-c] chinolin und seine Salze, Verfahren zur Herstellung derselben sowie diese Verbindungen enthaltende Arzneimittel
DE3438244C2 (fr)	1990-08-30
DE2814983A1 (de)	1979-10-18	Neue chromanon-derivate
DE3876925T2 (de)	1993-06-09	Kondensationsprodukte aus 2,2,4-trimethyl-1,2-dihydro-chinolin und oxoverbindungen und derivate daraus.
DE2502504B2 (de)	1979-05-10	Phenothiazinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
CH677490A5 (fr)	1991-05-31
DE1493618A1 (de)	1969-07-10	Cumarinderivate und ein Verfahren zu ihrer Herstellung
DE1206879B (de)	1965-12-16	Verfahren zur Herstellung von p-Aminoarylaldehyden
DE2414084A1 (de)	1974-10-03	Dinitroanilinderivate
EP0012725B1 (fr)	1984-02-29	Dérivés de Di-N-oxydes de quinoxaline, procédé pour leur préparation, compositions les contenant et leur application
AT215424B (de)	1961-06-12	Verfahren zur Herstellung von Xanthenen bzw. Thiaxanthenen
EP0070384A1 (fr)	1983-01-26	Benzotriazoles, leur préparation et leur application comme fongicides
DE971002C (de)	1958-11-27	Verfahren zur Herstellung von Thioxanthonen
DE1695414B2 (de)	1976-10-21	4-hydroxy-chinolin-3-carbonsaeureesterderivate, verfahren zu deren herstellung und beifuttermittel
DE825548C (de)	1951-12-20	Verfahren zur Herstellung von neuen diquartaeren Salzen von Pyrimidylaminocinnolinen
DE1695605A1 (de)	1972-02-24	Verfahren zur Herstellung von Chinoxalin-N,N'-dioxyden
DE1545672A1 (de)	1969-08-07	Dikarbonsaeureimidderivate und Verfahren zu ihrer Herstellung
DE850297C (de)	1952-09-22	Verfahren zur Herstellung von Amidinsalzen
DE3808355A1 (de)	1988-09-29	1-naphthoesaeure und deren funktionelle verbindungen, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel
DE1933523C (de)	1972-05-31	3-Benzal-thiochroman-4-on-l-oxide