NO744715L - - Google Patents
Info
- Publication number
- NO744715L NO744715L NO744715A NO744715A NO744715L NO 744715 L NO744715 L NO 744715L NO 744715 A NO744715 A NO 744715A NO 744715 A NO744715 A NO 744715A NO 744715 L NO744715 L NO 744715L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- formula
- naphthyridine
- ethyl
- oxo
- Prior art date
Links
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 26
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 22
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000005270 trialkylamine group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 150000001450 anions Chemical class 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 150000004820 halides Chemical class 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 claims description 5
- 150000005058 1,8-naphthyridines Chemical class 0.000 claims description 4
- 230000029936 alkylation Effects 0.000 claims description 4
- 238000005804 alkylation reaction Methods 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 claims description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 3
- 239000000575 pesticide Substances 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- MUDSDYNRBDKLGK-UHFFFAOYSA-N 4-methylquinoline Chemical compound C1=CC=C2C(C)=CC=NC2=C1 MUDSDYNRBDKLGK-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 150000008050 dialkyl sulfates Chemical class 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 125000004954 trialkylamino group Chemical group 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims 1
- 239000004476 plant protection product Substances 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 40
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 35
- 239000011630 iodine Substances 0.000 description 34
- 229910052740 iodine Inorganic materials 0.000 description 34
- 239000000203 mixture Substances 0.000 description 34
- -1 halide anion Chemical class 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 12
- 239000002585 base Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000013019 agitation Methods 0.000 description 5
- CYDFIAGFVIGXQJ-UHFFFAOYSA-N 1-ethyl-7-methyl-3-propanoyl-1,8-naphthyridin-4-one Chemical compound CC1=CC=C2C(=O)C(C(=O)CC)=CN(CC)C2=N1 CYDFIAGFVIGXQJ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- WIZNBODWFXTVAP-UHFFFAOYSA-N 1-ethyl-7-methyl-3-(2-methylpropanoyl)-1,8-naphthyridin-4-one Chemical compound C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(C(C)C)=O WIZNBODWFXTVAP-UHFFFAOYSA-N 0.000 description 3
- ZPVXFTFVNMMWJX-UHFFFAOYSA-N 1-ethyl-7-methyl-3-(3-phenylpropanoyl)-1,8-naphthyridin-4-one Chemical compound C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(CCC1=CC=CC=C1)=O ZPVXFTFVNMMWJX-UHFFFAOYSA-N 0.000 description 3
- FQDNITWZGPQXBT-UHFFFAOYSA-N 1-ethyl-7-methyl-3-pentanoyl-1,8-naphthyridin-4-one Chemical compound C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(CCCC)=O FQDNITWZGPQXBT-UHFFFAOYSA-N 0.000 description 3
- HVCZWSOWSDXARN-UHFFFAOYSA-N 3-(1,2-dimethylpyridin-1-ium-3-carbonyl)-7-methyl-1H-1,8-naphthyridin-4-one iodide Chemical compound [I-].CC1=CC=C2C(C(=CNC2=N1)C(=O)C=1C(=[N+](C=CC1)C)C)=O HVCZWSOWSDXARN-UHFFFAOYSA-N 0.000 description 3
- LSUQPHPXYPEBRM-UHFFFAOYSA-N 3-(2-bromo-2-methylpropanoyl)-1-ethyl-7-methyl-1,8-naphthyridin-4-one Chemical compound C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(C(C)(C)Br)=O LSUQPHPXYPEBRM-UHFFFAOYSA-N 0.000 description 3
- ICZPXVNCDPEYSR-UHFFFAOYSA-N 3-butanoyl-1-ethyl-7-methyl-1,8-naphthyridin-4-one Chemical compound C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(CCC)=O ICZPXVNCDPEYSR-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000007126 N-alkylation reaction Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- OTBBVGDVKUGFQK-UHFFFAOYSA-M [Br-].C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(=O)C1=C(C(=[N+](C=C1)C)C)C Chemical compound [Br-].C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(=O)C1=C(C(=[N+](C=C1)C)C)C OTBBVGDVKUGFQK-UHFFFAOYSA-M 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- KFDHIILYKICEGY-UHFFFAOYSA-M 1-ethyl-7-methyl-3-(1-methyl-2-phenylpyridin-1-ium-3-carbonyl)-1,8-naphthyridin-4-one iodide Chemical compound [I-].C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(=O)C=1C(=[N+](C=CC1)C)C1=CC=CC=C1 KFDHIILYKICEGY-UHFFFAOYSA-M 0.000 description 1
- NQUIRWXTTAMWIU-UHFFFAOYSA-N 1h-1,8-naphthyridin-4-one Chemical compound C1=CC=C2C(O)=CC=NC2=N1 NQUIRWXTTAMWIU-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- QUXLCYFNVNNRBE-UHFFFAOYSA-N 6-methylpyridin-2-amine Chemical compound CC1=CC=CC(N)=N1 QUXLCYFNVNNRBE-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XZOVCSPCZQGKJD-UHFFFAOYSA-N C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(CCC1CCCCC1)=O Chemical compound C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(CCC1CCCCC1)=O XZOVCSPCZQGKJD-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- ZZDGZJIFEMSRFR-UHFFFAOYSA-M [I-].C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(=O)C1=C(C(=[N+](C=C1)C)C)C Chemical compound [I-].C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(=O)C1=C(C(=[N+](C=C1)C)C)C ZZDGZJIFEMSRFR-UHFFFAOYSA-M 0.000 description 1
- MKCSZCVXAHYHQX-UHFFFAOYSA-M [I-].C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(=O)C=1C(=[N+](C=CC1)C)C Chemical group [I-].C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(=O)C=1C(=[N+](C=CC1)C)C MKCSZCVXAHYHQX-UHFFFAOYSA-M 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 1
- XDRMBCMMABGNMM-UHFFFAOYSA-N ethyl benzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=CC=C1 XDRMBCMMABGNMM-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 230000006203 ethylation Effects 0.000 description 1
- 238000006200 ethylation reaction Methods 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
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU73CI00001430A HU171561B (hu) | 1973-12-29 | 1973-12-29 | Sposob poluchenija proizvodnykh 1,8-naftiridina |
| JP49007604A JPS50100092A (de) | 1973-12-29 | 1974-01-17 | |
| HU74CI00001521A HU171868B (hu) | 1974-01-17 | 1974-12-04 | Sposob poluchenija novykh proizvodnykh 1,8-naftiridina |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO744715L true NO744715L (de) | 1975-07-28 |
Family
ID=27270157
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO744715A NO744715L (de) | 1973-12-29 | 1974-12-27 |
Country Status (13)
| Country | Link |
|---|---|
| AR (1) | AR207854A1 (de) |
| BG (1) | BG23898A3 (de) |
| CA (1) | CA1053234A (de) |
| CH (1) | CH617198A5 (de) |
| DD (1) | DD115905A5 (de) |
| DK (1) | DK677474A (de) |
| ES (1) | ES433690A1 (de) |
| FI (1) | FI375774A (de) |
| GB (1) | GB1493948A (de) |
| NL (1) | NL7416923A (de) |
| NO (1) | NO744715L (de) |
| SE (1) | SE7416321L (de) |
| SU (1) | SU567409A3 (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9023289D0 (en) * | 1990-10-25 | 1990-12-05 | Ici Plc | Herbicides |
-
1974
- 1974-01-01 AR AR257146A patent/AR207854A1/es active
- 1974-12-23 DK DK677474A patent/DK677474A/da not_active Application Discontinuation
- 1974-12-24 GB GB55871/74A patent/GB1493948A/en not_active Expired
- 1974-12-24 CH CH1730474A patent/CH617198A5/de not_active IP Right Cessation
- 1974-12-27 SE SE7416321A patent/SE7416321L/xx unknown
- 1974-12-27 NO NO744715A patent/NO744715L/no unknown
- 1974-12-27 SU SU742093429A patent/SU567409A3/ru active
- 1974-12-27 FI FI3757/74A patent/FI375774A/fi unknown
- 1974-12-27 NL NL7416923A patent/NL7416923A/xx not_active Application Discontinuation
- 1974-12-27 CA CA217,001A patent/CA1053234A/en not_active Expired
- 1974-12-28 ES ES433690A patent/ES433690A1/es not_active Expired
- 1974-12-30 BG BG7400030116A patent/BG23898A3/xx unknown
- 1974-12-30 DD DD183435A patent/DD115905A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES433690A1 (es) | 1977-04-16 |
| DK677474A (de) | 1975-09-01 |
| SU567409A3 (ru) | 1977-07-30 |
| DD115905A5 (de) | 1975-10-20 |
| SE7416321L (de) | 1975-06-30 |
| AR207854A1 (es) | 1976-11-08 |
| NL7416923A (nl) | 1975-07-01 |
| CH617198A5 (en) | 1980-05-14 |
| GB1493948A (en) | 1977-11-30 |
| CA1053234A (en) | 1979-04-24 |
| BG23898A3 (en) | 1977-11-10 |
| FI375774A (de) | 1975-06-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3330641A (en) | Herbicidal composition and method | |
| HUT64064A (en) | Process for producing puyrido/1,2-a/pyrimidine derivatives and pharmaceutical compositions comprising same as active ingredient | |
| US3767667A (en) | Process for preparing 1h-tetrazole compounds | |
| NO762661L (de) | ||
| US3564606A (en) | 3-amino-5-halogenated aryloxymethyl-1,2,4-oxadiazoles | |
| US3853898A (en) | 3-(2-substituted amino) pyridyl-phenyl ketone imines | |
| US3907824A (en) | Preparation of 1-alkyl-3,5-diphenylpyrazoles and 1,2-dialkyl-3,5-diphenylpyrazolium salts | |
| NO744715L (de) | ||
| US3635995A (en) | 2-(2-imidazolin-2-yl)methylthiopyridine-n-oxide and derivatives thereof | |
| US2970154A (en) | Amino derivative | |
| Elnagdi et al. | Reactions with cyclic amidines II. The behaviour of cyclic amidines toward ethoxycarbonyl and aroyl isothiocyanates | |
| US3382246A (en) | Certain 3-(2'-pyridyl)-4(3h)-quinazolones | |
| US3546220A (en) | 2,3-dihydro-1h-pyrido-(2,3-b)(1,4)thiazines | |
| US3923822A (en) | 6-fluoro-3,5-dihalo-2-pyridinols | |
| US4610990A (en) | 5-(1-cyano-1-alkyl-N-methyl-N-methoxy-phenethyl)-alkylamino-2,2,8-trimethyl-4H-dioxino-(4,5-c)-pyridine derivatives, and their use as calcium antagonistic agents | |
| EP0324920B1 (de) | Verfahren zur Herstellung von Thiotepa | |
| EP0181636B1 (de) | 5-Cyanopyridine-2-diazohydroxide, basische Salze und Verfahren zu ihrer Herstellung und Anwendung | |
| CA1089855A (en) | Derivatives of pyrazolo [1,5-a] pyrido [2,3- d]-pyrimidin-9(4h)-one | |
| SU1082324A3 (ru) | Способ получени конденсированных производных пиримидина или их солей | |
| NO744716L (de) | ||
| US2690441A (en) | 3-carboline derivatives | |
| GB2080291A (en) | 6-Hydrazono-pyrido[2,1- b]quinazolin-11-ones, the salts thereof and processes for their preparation | |
| EP0945434B1 (de) | Verfahren zur herstellung von halogenierten heteroarylverbindungen | |
| AT340943B (de) | Verfahren zur herstellung von neuen 1,8-naphthyridin-derivaten | |
| US3042676A (en) | Pyridinium quaternary salts and methods of preparing the same |