HU182010B - Novel 2,2-dimethyl-1,2-dihydro-quinoline derivatives having anti-oxidant activity - Google Patents
Novel 2,2-dimethyl-1,2-dihydro-quinoline derivatives having anti-oxidant activity Download PDFInfo
- Publication number
- HU182010B HU182010B HU79CI1916A HUCI001916A HU182010B HU 182010 B HU182010 B HU 182010B HU 79CI1916 A HU79CI1916 A HU 79CI1916A HU CI001916 A HUCI001916 A HU CI001916A HU 182010 B HU182010 B HU 182010B
- Authority
- HU
- Hungary
- Prior art keywords
- dimethyl
- sulfonic acid
- acid
- dihydroquinoline
- salts
- Prior art date
Links
- 230000003078 antioxidant effect Effects 0.000 title description 7
- JWSUYSBONRNZRW-UHFFFAOYSA-N 2,2-dimethyl-1h-quinoline Chemical class C1=CC=C2C=CC(C)(C)NC2=C1 JWSUYSBONRNZRW-UHFFFAOYSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 4
- IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical compound C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 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 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 4
- IHBCFWWEZXPPLG-UHFFFAOYSA-N [Ca].[Zn] Chemical compound [Ca].[Zn] IHBCFWWEZXPPLG-UHFFFAOYSA-N 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 abstract description 11
- 150000001875 compounds Chemical class 0.000 abstract description 10
- GUNHIIHGOPJGMO-UHFFFAOYSA-N (2,2-dimethyl-1h-quinolin-4-yl)methanesulfonic acid Chemical compound C1=CC=C2C(CS(O)(=O)=O)=CC(C)(C)NC2=C1 GUNHIIHGOPJGMO-UHFFFAOYSA-N 0.000 abstract description 5
- 150000003751 zinc Chemical class 0.000 abstract description 3
- 230000003647 oxidation Effects 0.000 abstract description 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 239000013543 active substance Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 9
- 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 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- -1 2,2-dimethyl-1,2-dihydroquinoline-4-yl Chemical group 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- ZDPALFHDPFYJDY-UHFFFAOYSA-N [Na].OC=O Chemical compound [Na].OC=O ZDPALFHDPFYJDY-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000003811 acetone extraction Methods 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 description 1
- 238000002224 dissection Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229940096992 potassium oleate Drugs 0.000 description 1
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- CBXWGGFGZDVPNV-UHFFFAOYSA-N so4-so4 Chemical compound OS(O)(=O)=O.OS(O)(=O)=O CBXWGGFGZDVPNV-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- QZSGYPOMAGZIOZ-UHFFFAOYSA-M sodium;(2,2-dimethyl-1h-quinolin-4-yl)methanesulfonate Chemical compound [Na+].C1=CC=C2C(CS([O-])(=O)=O)=CC(C)(C)NC2=C1 QZSGYPOMAGZIOZ-UHFFFAOYSA-M 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- C07D215/12—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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23B2/00—Preservation of foods or foodstuffs, in general
- A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
- A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
- A23B2/729—Organic compounds; Microorganisms; Enzymes
-
- 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
- A23K20/132—Heterocyclic compounds containing only one nitrogen as hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Food Science & Technology (AREA)
- Wood Science & Technology (AREA)
- Animal Husbandry (AREA)
- Fodder In General (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Quinoline Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Fats And Perfumes (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (28)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79CI1916A HU182010B (en) | 1979-02-21 | 1979-02-21 | Novel 2,2-dimethyl-1,2-dihydro-quinoline derivatives having anti-oxidant activity |
| SE8001235A SE452319B (sv) | 1979-02-21 | 1980-02-15 | 2,2-dimetyl-1,2-dihydrokinolinderivat anvendbara som antioxidanter, jemte sett for deras framstellning och anvendning derav i nerings- eller foderblandningar |
| US06/121,810 US4363910A (en) | 1979-02-21 | 1980-02-15 | 2,2-Dimethyl-1,2-dihydroquinoline derivatives useful as antioxidants |
| DE19803005874 DE3005874A1 (de) | 1979-02-21 | 1980-02-16 | Neues antioxydans |
| IL59406A IL59406A (en) | 1979-02-21 | 1980-02-18 | (2,2-dimethyl-1,2-dihydroquinol-4-yl)methylsulfonic acid and salts thereof,their preparation and antioxidant compositions containing them |
| FR8003617A FR2449681A1 (fr) | 1979-02-21 | 1980-02-19 | Derives de 2,2-dimethyl-1,2-dihydroquinoleine utiles comme anti-oxydants, procede pour leur preparation, et melanges qui les contiennent |
| NL8001019A NL8001019A (nl) | 1979-02-21 | 1980-02-20 | Als anti oxydanten te gebruiken 2,2-dimethyl-1,2- -dihydrochinolinederivaten, werkwijze voor het bereiden daarvan en mengsels, die ze bevatten. |
| PL1980222117A PL123145B1 (en) | 1979-02-21 | 1980-02-20 | Process for preparing novel /2,2-dimethyl-1,2-dihydroquinolinyl-4/-methylsulfonic acid and its salts and fodder composition containing this compound |
| GB8005722A GB2044258B (en) | 1979-02-21 | 1980-02-20 | Quinoline derivatives useful as antioxidants their preparation and compositions containing them |
| SU802884428A SU888818A3 (ru) | 1979-02-21 | 1980-02-20 | Способ получени (2,2-диметил-1,2-дигидрохинолин-4-ил)-метилусульфокислоты или ее солей |
| DK073880A DK152286C (da) | 1979-02-21 | 1980-02-20 | (2,2-dimethyl-1,2-dihydroquinolin-4-yl)-methyl-sulfonsyre eller alkalimetal-, jordalkalimetal- eller ammoniumsalte deraf samt blandinger indeholdende disse forbindelser som antioxidanter |
| ES489372A ES489372A0 (es) | 1979-02-21 | 1980-02-20 | Procedimiento para preparar nuevos derivados de 2,2-dime- til-1,2-dihidroquinolina |
| FI800499A FI76566C (fi) | 1979-02-21 | 1980-02-20 | (2,2-dimetyl-1,2-dihydrokinolin-4-yl) metylsulfonsyra och salter daerav anvaendbara som antioxidanter, foerfarande foer deras framstaellning och blandningar innehaollande dessa. |
| YU454/80A YU41697B (en) | 1979-02-21 | 1980-02-20 | Process for producing 2,2-dimethyl-1,2-dimethyl-1,2-dihydroguinoline derivatives used as antioxidates |
| CH137780A CH644104A5 (de) | 1979-02-21 | 1980-02-20 | (2,2-dimethyl-1,2-dihydro-chinolin-4-yl)-methyl-sulfonsaeure und salze derselben, verfahren zu ihrer herstellung und ihre verwendung als antioxydans. |
| BG8046707A BG35240A1 (en) | 1979-02-21 | 1980-02-21 | (2, 2- dimethyl- 1, 2- dihydroquinoline- 4- yl)- methylsulphonic acid, its salts and their use |
| JP1980780A JPS55115870A (en) | 1979-02-21 | 1980-02-21 | 2*22dimethyll1*22dihydroquinoline derivative and its manufacture and use |
| CS801207A CS229654B2 (en) | 1979-02-21 | 1980-02-21 | Manufacturing process of /2,2 dimethyl -1,2-dihydro chinolin 4-yl/methylsulfon acid and its salt. |
| BE0/199484A BE881836A (fr) | 1979-02-21 | 1980-02-21 | Derives de 2,2-dimethyl-1,2-dihydroquinoleine utiles comme anti-oxydants, procede pour leur preparation et melanges qui les contiennent |
| BG046706A BG33280A3 (bg) | 1979-02-21 | 1980-02-21 | Метод за получаване на (2, 2- диметил- 1, 2- хидрохинолин- 4- ил)- метилсулфонова киселина и нейни соли |
| IT67268/80A IT1128235B (it) | 1979-02-21 | 1980-02-21 | Derivati di 2 2 dimetil 1 2 diidro chinolina utili come antiossidanti procedimento per la loro preparazione e miscele che li contengono |
| RO80100263A RO78158A (ro) | 1979-02-21 | 1980-02-21 | Procedeu pentru prepararea acidului (2,2-dimetil-1,2-dihidrochinolin-4-il)-metilsulfonic |
| BR8001025A BR8001025A (pt) | 1979-02-21 | 1980-02-21 | Derivados de 2,2-dimetila-1,2-diidroquinolina, processo para o preparo de acido metilsulfonico (2,2-dimetila-1,2-diidroquinolina-4-1l) e os seus sais, misturas que contem substancias sensiveis a oxidacao, nitrimentos e/ou misturas de forragem, pre-misturas anti-oxidantes, misturas graxas anti-oxidantes, processos para o preparo dessas misturas |
| CA000346187A CA1138876A (en) | 1979-02-21 | 1980-02-21 | 2,2-dimethyl-1,2-dihydroquinoline derivatives useful as antioxidants, a process for the preparation thereof and mixtures containing them |
| AT0095880A AT375069B (de) | 1979-02-21 | 1980-02-21 | Verfahren zur herstellung der (2,2-dimethyl-1,2dihydro-chinolin-4-yl)-methyl-sulfon-s[ure und von deren salzen |
| SU802937194A SU975710A1 (ru) | 1979-02-21 | 1980-06-25 | (2,2-Диметил-1,2-дигидрохинолин-4-ил)метилсульфокислота или ее натриева соль, как антиокислитель в добавках к кормам |
| CS812357A CS229661B2 (cs) | 1979-02-21 | 1981-03-30 | Krmné směsi obsahující látky citlivé na oxidaci, respektive předsměsi k jejich vytvoření |
| US06/353,380 US4490394A (en) | 1979-02-21 | 1982-03-01 | 2,2-Dimethyl-1,2-dihydroquinoline derivatives useful as antioxidants, a process for the preparation thereof and mixtures containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79CI1916A HU182010B (en) | 1979-02-21 | 1979-02-21 | Novel 2,2-dimethyl-1,2-dihydro-quinoline derivatives having anti-oxidant activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU182010B true HU182010B (en) | 1983-12-28 |
Family
ID=10994739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79CI1916A HU182010B (en) | 1979-02-21 | 1979-02-21 | Novel 2,2-dimethyl-1,2-dihydro-quinoline derivatives having anti-oxidant activity |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4363910A (en, 2012) |
| JP (1) | JPS55115870A (en, 2012) |
| AT (1) | AT375069B (en, 2012) |
| BE (1) | BE881836A (en, 2012) |
| BG (2) | BG33280A3 (en, 2012) |
| BR (1) | BR8001025A (en, 2012) |
| CA (1) | CA1138876A (en, 2012) |
| CH (1) | CH644104A5 (en, 2012) |
| CS (1) | CS229654B2 (en, 2012) |
| DE (1) | DE3005874A1 (en, 2012) |
| DK (1) | DK152286C (en, 2012) |
| ES (1) | ES489372A0 (en, 2012) |
| FI (1) | FI76566C (en, 2012) |
| FR (1) | FR2449681A1 (en, 2012) |
| GB (1) | GB2044258B (en, 2012) |
| HU (1) | HU182010B (en, 2012) |
| IL (1) | IL59406A (en, 2012) |
| IT (1) | IT1128235B (en, 2012) |
| NL (1) | NL8001019A (en, 2012) |
| PL (1) | PL123145B1 (en, 2012) |
| RO (1) | RO78158A (en, 2012) |
| SE (1) | SE452319B (en, 2012) |
| SU (2) | SU888818A3 (en, 2012) |
| YU (1) | YU41697B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK328483D0 (da) * | 1983-07-15 | 1983-07-15 | Magius N W Von | Ethoxyquinsalte |
| GB8816269D0 (en) * | 1988-07-08 | 1988-08-10 | Int Assn Of Fish Meal Manufact | Compounds for use as anti-oxidants in fish meal/fish oil |
| 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 |
| MXPA05006544A (es) * | 2002-12-18 | 2005-08-16 | Ciba Sc Holding Ag | Antioxidantes para grasas, aceites y alimento. |
| DE10329860A1 (de) | 2003-07-02 | 2005-01-20 | Atto-Tec Gmbh | Sulfonamidderivate polycyclischer Farbstoffe für analytische Anwendungen |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2562970A (en) * | 1950-04-14 | 1951-08-07 | Thompson Chester Ray | Preservation of forage crops |
| US3024217A (en) * | 1959-06-25 | 1962-03-06 | Firestone Tire & Rubber Co | Rubber antioxidant |
| DE1492900A1 (en, 2012) * | 1963-08-07 | 1970-08-27 | ||
| US3347677A (en) * | 1966-04-01 | 1967-10-17 | Monsanto Co | Activated dihydroquinolines |
-
1979
- 1979-02-21 HU HU79CI1916A patent/HU182010B/hu not_active IP Right Cessation
-
1980
- 1980-02-15 US US06/121,810 patent/US4363910A/en not_active Expired - Lifetime
- 1980-02-15 SE SE8001235A patent/SE452319B/sv not_active IP Right Cessation
- 1980-02-16 DE DE19803005874 patent/DE3005874A1/de active Granted
- 1980-02-18 IL IL59406A patent/IL59406A/xx unknown
- 1980-02-19 FR FR8003617A patent/FR2449681A1/fr active Granted
- 1980-02-20 ES ES489372A patent/ES489372A0/es active Granted
- 1980-02-20 CH CH137780A patent/CH644104A5/de not_active IP Right Cessation
- 1980-02-20 PL PL1980222117A patent/PL123145B1/pl unknown
- 1980-02-20 FI FI800499A patent/FI76566C/fi not_active IP Right Cessation
- 1980-02-20 YU YU454/80A patent/YU41697B/xx unknown
- 1980-02-20 NL NL8001019A patent/NL8001019A/nl not_active Application Discontinuation
- 1980-02-20 GB GB8005722A patent/GB2044258B/en not_active Expired
- 1980-02-20 DK DK073880A patent/DK152286C/da active
- 1980-02-20 SU SU802884428A patent/SU888818A3/ru active
- 1980-02-21 CA CA000346187A patent/CA1138876A/en not_active Expired
- 1980-02-21 AT AT0095880A patent/AT375069B/de not_active IP Right Cessation
- 1980-02-21 CS CS801207A patent/CS229654B2/cs unknown
- 1980-02-21 RO RO80100263A patent/RO78158A/ro unknown
- 1980-02-21 IT IT67268/80A patent/IT1128235B/it active
- 1980-02-21 BG BG046706A patent/BG33280A3/xx unknown
- 1980-02-21 BG BG8046707A patent/BG35240A1/xx unknown
- 1980-02-21 BR BR8001025A patent/BR8001025A/pt unknown
- 1980-02-21 JP JP1980780A patent/JPS55115870A/ja active Granted
- 1980-02-21 BE BE0/199484A patent/BE881836A/fr not_active IP Right Cessation
- 1980-06-25 SU SU802937194A patent/SU975710A1/ru active
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |