CA2029838C - Process for the preparation of aminotriazine derivatives - Google Patents
Process for the preparation of aminotriazine derivatives Download PDFInfo
- Publication number
- CA2029838C CA2029838C CA002029838A CA2029838A CA2029838C CA 2029838 C CA2029838 C CA 2029838C CA 002029838 A CA002029838 A CA 002029838A CA 2029838 A CA2029838 A CA 2029838A CA 2029838 C CA2029838 C CA 2029838C
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- formula
- substituted
- methyl
- radicals
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 title abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- -1 methoxy, methylthio Chemical group 0.000 claims abstract description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 7
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims abstract description 6
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 238000005903 acid hydrolysis reaction Methods 0.000 claims abstract description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 10
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims abstract 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 3
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000007858 starting material Substances 0.000 abstract description 8
- 239000000575 pesticide Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- OFUCCBIWEUKISP-UHFFFAOYSA-N 2,2,2-trifluoroacetohydrazide Chemical compound NNC(=O)C(F)(F)F OFUCCBIWEUKISP-UHFFFAOYSA-N 0.000 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- IFLRITVIVMSVTL-UHFFFAOYSA-N 4-amino-2,5-dihydro-1,2,4-triazin-3-one Chemical class NN1CC=NNC1=O IFLRITVIVMSVTL-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000002826 nitrites Chemical class 0.000 description 3
- 238000006049 ring expansion reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CFSKCSYBGMQIRX-UHFFFAOYSA-N O=C(N1N=C(C(F)(F)F)OC1=O)N1N=C(C(F)(F)F)OC1=O Chemical class O=C(N1N=C(C(F)(F)F)OC1=O)N1N=C(C(F)(F)F)OC1=O CFSKCSYBGMQIRX-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical group C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- OEPCSIUNTBHPGP-UHFFFAOYSA-N 2-(2-amino-5-methyl-1,3,4-oxadiazol-3-ium-3-yl)-1-phenylethanone;bromide Chemical compound [Br-].O1C(C)=N[N+](CC(=O)C=2C=CC=CC=2)=C1N OEPCSIUNTBHPGP-UHFFFAOYSA-N 0.000 description 1
- OLVGIDBBKFEUSQ-UHFFFAOYSA-N 3-(2-oxo-1,3,4-oxadiazole-3-carbonyl)-1,3,4-oxadiazol-2-one Chemical class O1C(N(N=C1)C(=O)N1C(OC=N1)=O)=O OLVGIDBBKFEUSQ-UHFFFAOYSA-N 0.000 description 1
- PZWSJMODMCELST-UHFFFAOYSA-N 4-[methyl(pyridin-3-yl)amino]-2,5-dihydro-1,2,4-triazin-3-one Chemical class C=1C=CN=CC=1N(C)N1CC=NNC1=O PZWSJMODMCELST-UHFFFAOYSA-N 0.000 description 1
- WBEADNOHWGGYHE-UHFFFAOYSA-N 4-[methyl(pyridin-3-yl)amino]-6-propan-2-yl-2,5-dihydro-1,2,4-triazin-3-one Chemical compound C1C(C(C)C)=NNC(=O)N1N(C)C1=CC=CN=C1 WBEADNOHWGGYHE-UHFFFAOYSA-N 0.000 description 1
- OGCQMAVVZPWFHR-UHFFFAOYSA-N 4-amino-6-phenyl-2,5-dihydro-1,2,4-triazin-3-one Chemical class N1C(=O)N(N)CC(C=2C=CC=CC=2)=N1 OGCQMAVVZPWFHR-UHFFFAOYSA-N 0.000 description 1
- WBAFTNAJPQGNME-UHFFFAOYSA-N 5-(trifluoromethyl)-3h-1,3,4-oxadiazol-2-one Chemical compound OC1=NN=C(C(F)(F)F)O1 WBAFTNAJPQGNME-UHFFFAOYSA-N 0.000 description 1
- NNXROHRFMWHXNH-UHFFFAOYSA-N 5-methyl-3h-1,3,4-oxadiazol-2-one Chemical compound CC1=NN=C(O)O1 NNXROHRFMWHXNH-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 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
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005283 haloketone group Chemical group 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- NCSCAWXVGUIUEY-UHFFFAOYSA-N n-(6-methyl-3-oxo-2,5-dihydro-1,2,4-triazin-4-yl)acetamide Chemical compound CC(=O)NN1CC(C)=NNC1=O NCSCAWXVGUIUEY-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical class O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002320676A CA2320676C (en) | 1989-11-15 | 1990-11-13 | Process and intermediates for the preparation of aminotriazine derivatives |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH4107/89-7 | 1989-11-15 | ||
| CH410789 | 1989-11-15 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002320676A Division CA2320676C (en) | 1989-11-15 | 1990-11-13 | Process and intermediates for the preparation of aminotriazine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2029838A1 CA2029838A1 (en) | 1991-05-16 |
| CA2029838C true CA2029838C (en) | 2001-06-19 |
Family
ID=4269949
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002320676A Expired - Lifetime CA2320676C (en) | 1989-11-15 | 1990-11-13 | Process and intermediates for the preparation of aminotriazine derivatives |
| CA002029838A Expired - Lifetime CA2029838C (en) | 1989-11-15 | 1990-11-13 | Process for the preparation of aminotriazine derivatives |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002320676A Expired - Lifetime CA2320676C (en) | 1989-11-15 | 1990-11-13 | Process and intermediates for the preparation of aminotriazine derivatives |
Country Status (14)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9304178D0 (en) * | 1993-03-02 | 1993-04-21 | Ciba Geigy Ag | Process for the preparation of 6-alkyl-4-(pyridin-3-yl-methyleneamino),5-dihydro-1,2,4-triazin-3(2h)-one |
| US5384403A (en) * | 1993-03-31 | 1995-01-24 | Ciba-Geigy Corporation | Process for the preparation of aminotriazine derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5416515B1 (enrdf_load_stackoverflow) * | 1968-08-19 | 1979-06-22 | ||
| JPS6011478A (ja) * | 1983-06-30 | 1985-01-21 | Showa Denko Kk | オキサジアゾリノン誘導体及び除草剤 |
| US4699647A (en) * | 1985-05-30 | 1987-10-13 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| ATE121742T1 (de) * | 1987-10-16 | 1995-05-15 | Ciba Geigy Ag | Schädlingsbekämpfungsmittel. |
-
1990
- 1990-10-24 TW TW079108994A patent/TW199149B/zh active
- 1990-11-06 SG SG1996001138A patent/SG43813A1/en unknown
- 1990-11-06 ES ES90810853T patent/ES2091815T3/es not_active Expired - Lifetime
- 1990-11-06 DK DK90810853.3T patent/DK0433218T3/da not_active Application Discontinuation
- 1990-11-06 DE DE59010496T patent/DE59010496D1/de not_active Expired - Lifetime
- 1990-11-06 EP EP90810853A patent/EP0433218B1/de not_active Expired - Lifetime
- 1990-11-08 IL IL11161790A patent/IL111617A/en not_active IP Right Cessation
- 1990-11-08 IL IL9628090A patent/IL96280A/en not_active IP Right Cessation
- 1990-11-13 CA CA002320676A patent/CA2320676C/en not_active Expired - Lifetime
- 1990-11-13 CA CA002029838A patent/CA2029838C/en not_active Expired - Lifetime
- 1990-11-14 KR KR1019900018447A patent/KR0150208B1/ko not_active Expired - Lifetime
- 1990-11-14 IE IE411390A patent/IE73669B1/en not_active IP Right Cessation
- 1990-11-14 ZA ZA909120A patent/ZA909120B/xx unknown
- 1990-11-14 PT PT95888A patent/PT95888B/pt not_active IP Right Cessation
- 1990-11-15 JP JP2310158A patent/JP2943010B2/ja not_active Expired - Lifetime
-
1994
- 1994-11-14 IL IL11161794A patent/IL111617A0/xx unknown
-
1996
- 1996-09-12 GR GR960402339T patent/GR3020992T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT95888A (pt) | 1991-09-13 |
| JPH03188070A (ja) | 1991-08-16 |
| IL96280A0 (en) | 1991-08-16 |
| IL96280A (en) | 1996-01-31 |
| KR0150208B1 (ko) | 1998-10-15 |
| IE73669B1 (en) | 1997-07-02 |
| CA2029838A1 (en) | 1991-05-16 |
| PT95888B (pt) | 1997-11-28 |
| EP0433218A1 (de) | 1991-06-19 |
| KR910009677A (ko) | 1991-06-28 |
| ZA909120B (en) | 1991-07-31 |
| SG43813A1 (en) | 1997-11-14 |
| EP0433218B1 (de) | 1996-09-11 |
| IL111617A (en) | 1996-05-14 |
| JP2943010B2 (ja) | 1999-08-30 |
| ES2091815T3 (es) | 1996-11-16 |
| CA2320676A1 (en) | 1991-05-16 |
| DK0433218T3 (da) | 1996-09-30 |
| GR3020992T3 (en) | 1996-12-31 |
| IE904113A1 (en) | 1991-05-22 |
| DE59010496D1 (de) | 1996-10-17 |
| CA2320676C (en) | 2004-11-02 |
| TW199149B (enrdf_load_stackoverflow) | 1993-02-01 |
| IL111617A0 (en) | 1995-01-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0714925B2 (ja) | ヘテロアリールオキシアセトアミドの製法 | |
| US4175188A (en) | Process for the production of 1,2,4-triazin-5-one derivatives | |
| US5648487A (en) | Process for the preparation of aminotriazine derivatives | |
| US5561230A (en) | Process for the preparation of aminotriazine derivatives | |
| CA2029838C (en) | Process for the preparation of aminotriazine derivatives | |
| US9663490B2 (en) | Process for making reverse transcriptase inhibitors | |
| Steiner et al. | Synthesis and antihypertensive activity of new 6-heteroaryl-3-hydrazinopyridazine derivatives | |
| EP0322401B1 (en) | Tetrahydrophthalimide derivatives, their production and use | |
| HU225477B1 (en) | Process and new intermediates for the preparation of triazolinon-derivatives | |
| Baryshnikova et al. | The base-induced cascade rearrangement of 4-acetylamino-3-arylazo-1, 2, 5-oxadiazole 2-oxides (furoxans) into 4-acetylamino-2-aryl-5-nitro-2 H-1, 2, 3-triazoles | |
| NO811667L (no) | Fremgangsmaate ved fremstilling av substituerte pyrazinyl-1,2,4-oxadiazoler | |
| US3879386A (en) | Amino substituted 1,2,4-triazinones | |
| US3122537A (en) | Novel 6-phenyl dihydro-oxadiazines and method of preparation thereof | |
| Cartwright et al. | Gas-phase pyrolysis of 4-amino-3-allylthio-1, 2, 4-triazoles: a new route to [1, 3] thiazolo [3, 2-b][1, 2, 4] triazoles | |
| US5227392A (en) | Alkoxycoumarins substituted by a heterocyclic radical, their preparation and therapeutic agents containing these compounds | |
| SRIVASTAVA et al. | Synthesis of new 5, 3/5 and 2-substituted (1, 3, 4)-oxadiazoles and their related products as potential antifungal and antiviral agents | |
| JPH07196630A (ja) | トリアゾリノンの製造方法及び新規な中間体 | |
| CA1181406A (en) | 3,5-diphenyl-h-1,2,4-triazoles with contragestational activity, pharmaceutical compositions thereof and process for their preparation | |
| US3746719A (en) | 4-substituted 2-amino-1,3,4-thiadiazolones-(5) and process for their preparation | |
| KR20200088570A (ko) | 피마살탄 및 그의 제조 중간체의 제조방법 | |
| EP0088128A1 (en) | Antiinflammatory and analgetic 4-pyridylpyridazin(2h)-3-ones | |
| CA1044240A (en) | Process for the preparation of 2-arylamino-2-imidazoline derivatives | |
| CA2073064A1 (en) | (hetero) 4-arylmethoxy phenyl diazole derivatives, method for preparing same and their therapeutical applications | |
| HUT59674A (en) | Process for producing new 5-/ph+noxy-alkanoyl-amino/-uracyl derivatives and pharmaceutical compositions contaiing them | |
| US3471487A (en) | 3-((halophenoxy)methyl)-as-triazine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |