LV11463B - Process for the preparation of substituted 4,6-diamino-5-cyanopyrimidines - Google Patents
Process for the preparation of substituted 4,6-diamino-5-cyanopyrimidines Download PDFInfo
- Publication number
- LV11463B LV11463B LVP-96-53A LV960053A LV11463B LV 11463 B LV11463 B LV 11463B LV 960053 A LV960053 A LV 960053A LV 11463 B LV11463 B LV 11463B
- Authority
- LV
- Latvia
- Prior art keywords
- formula
- water
- mixture
- alkali metal
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 60
- 238000002360 preparation method Methods 0.000 title claims description 16
- BTVHLEVGNAQTBN-UHFFFAOYSA-N 4,6-diaminopyrimidine-5-carbonitrile Chemical class NC1=NC=NC(N)=C1C#N BTVHLEVGNAQTBN-UHFFFAOYSA-N 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 101
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 87
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 77
- 238000006243 chemical reaction Methods 0.000 claims description 72
- 239000000203 mixture Substances 0.000 claims description 59
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 45
- 239000002904 solvent Substances 0.000 claims description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 39
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 36
- 229910021529 ammonia Inorganic materials 0.000 claims description 35
- 159000000000 sodium salts Chemical class 0.000 claims description 33
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 150000001412 amines Chemical class 0.000 claims description 23
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 23
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 23
- -1 alkali metal salt Chemical class 0.000 claims description 22
- 150000003333 secondary alcohols Chemical class 0.000 claims description 22
- SSBDGGIFOJKRTP-UHFFFAOYSA-N 4,6-diamino-2-chloropyrimidine-5-carbonitrile Chemical compound NC1=NC(Cl)=NC(N)=C1C#N SSBDGGIFOJKRTP-UHFFFAOYSA-N 0.000 claims description 19
- 150000001768 cations Chemical class 0.000 claims description 19
- 239000002798 polar solvent Substances 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 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 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 7
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 6
- 239000012467 final product Substances 0.000 claims description 6
- 150000002894 organic compounds Chemical class 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 150000003950 cyclic amides Chemical class 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 5
- 229910052751 metal Inorganic materials 0.000 claims 3
- 239000002184 metal Substances 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 239000003513 alkali Substances 0.000 description 44
- 239000011541 reaction mixture Substances 0.000 description 41
- 239000000243 solution Substances 0.000 description 38
- 239000000047 product Substances 0.000 description 35
- 238000003556 assay Methods 0.000 description 31
- 239000007787 solid Substances 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 26
- 238000013019 agitation Methods 0.000 description 21
- 238000001914 filtration Methods 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 17
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 14
- 239000002002 slurry Substances 0.000 description 14
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 239000002585 base Substances 0.000 description 9
- 239000003518 caustics Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- PKTIFYGCWCQRSX-UHFFFAOYSA-N 4,6-diamino-2-(cyclopropylamino)pyrimidine-5-carbonitrile Chemical compound NC1=C(C#N)C(N)=NC(NC2CC2)=N1 PKTIFYGCWCQRSX-UHFFFAOYSA-N 0.000 description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- UMXIANHOYHXWIQ-UHFFFAOYSA-N (1-amino-2,2-dicyanoethenyl)cyanamide Chemical group N#CNC(N)=C(C#N)C#N UMXIANHOYHXWIQ-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 238000005915 ammonolysis reaction Methods 0.000 description 4
- 239000000010 aprotic solvent Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 229940113088 dimethylacetamide Drugs 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- 229940093475 2-ethoxyethanol Drugs 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000003760 magnetic stirring Methods 0.000 description 3
- 239000003586 protic polar solvent Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 description 2
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 2
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 description 1
- ISTJMQSHILQAEC-UHFFFAOYSA-N 2-methyl-3-pentanol Chemical compound CCC(O)C(C)C ISTJMQSHILQAEC-UHFFFAOYSA-N 0.000 description 1
- HYKZMKUYWOYQAZ-UHFFFAOYSA-N 4,6-diamino-2-ethoxypyrimidine-5-carbonitrile Chemical compound CCOC1=NC(N)=C(C#N)C(N)=N1 HYKZMKUYWOYQAZ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001409 amidines Chemical class 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
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- JWEKFMCYIRVOQZ-UHFFFAOYSA-N cyanamide;sodium Chemical compound [Na].NC#N JWEKFMCYIRVOQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002463 imidates Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9714193A | 1993-07-26 | 1993-07-26 | |
| US21098094A | 1994-03-21 | 1994-03-21 | |
| PCT/EP1994/002312 WO1995003282A2 (en) | 1993-07-26 | 1994-07-14 | Process for the preparation of substituted 4,6-diamino-5-cyanopyrimidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LV11463A LV11463A (lv) | 1996-08-20 |
| LV11463B true LV11463B (en) | 1996-12-20 |
Family
ID=26792702
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LVP-96-53A LV11463B (en) | 1993-07-26 | 1996-02-26 | Process for the preparation of substituted 4,6-diamino-5-cyanopyrimidines |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0711285A1 (cs) |
| JP (1) | JPH09500632A (cs) |
| CN (1) | CN1128024A (cs) |
| AU (1) | AU7385994A (cs) |
| BG (1) | BG100366A (cs) |
| BR (1) | BR9407024A (cs) |
| CA (1) | CA2166989A1 (cs) |
| CZ (1) | CZ22496A3 (cs) |
| FI (1) | FI960332A0 (cs) |
| HU (1) | HUT73357A (cs) |
| IL (1) | IL110425A0 (cs) |
| LV (1) | LV11463B (cs) |
| NO (1) | NO960307L (cs) |
| SK (1) | SK10396A3 (cs) |
| WO (1) | WO1995003282A2 (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6255316B1 (en) * | 1997-08-27 | 2001-07-03 | Novartis Animal Health Us, Inc. | Dicyclanil polymorphs and hydrates and their preparation |
| US8273899B2 (en) | 2007-04-19 | 2012-09-25 | Nippon Soda Co., Ltd. | Method for production of N-(2-amino-1,2-dicyanovinyl)imidates, method for production of N-(2-amino-1,2-dicyanovinyl)formamidine, and method for production of aminoimidazole derivatives |
| CN102250017A (zh) * | 2011-06-15 | 2011-11-23 | 扬州天和药业有限公司 | 地昔尼尔的一种合成方法 |
| CN102399193A (zh) * | 2011-12-15 | 2012-04-04 | 连云港市亚晖医药化工有限公司 | 4,6-二氨基-2-环丙胺基-5-腈基嘧啶的制备方法 |
| CN104130197A (zh) * | 2014-07-29 | 2014-11-05 | 华中农业大学 | 2,4,6-三氨基-5-氰基嘧啶的化学合成方法 |
| CN104649982B (zh) * | 2015-02-26 | 2016-12-07 | 齐鲁晟华制药有限公司 | 一种地昔尼尔的制备方法 |
| CN107056655B (zh) * | 2017-01-22 | 2018-12-04 | 营口三征新科技化工有限公司 | 一种1-氨基-1-氰氨基-2,2-二氰乙烯钠盐的制备方法 |
| CN106966922B (zh) * | 2017-03-28 | 2020-10-27 | 中国科学院大学 | 一种功能化取代的二氰基乙烯类化合物的合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1135913B (de) * | 1960-11-08 | 1962-09-06 | Bayer Ag | Verfahren zur Herstellung von 2-Methyl-4-amino-5-cyanpyrimidin |
| US3226424A (en) * | 1962-10-03 | 1965-12-28 | Hoffmann La Roche | Process for preparing 2-lower alkoxy-1,1-dicyanoethylene and 2-amino-1,1-dicyanoethylene |
| US4783468A (en) * | 1986-04-30 | 1988-11-08 | Ciba-Geigy Corporation | Insecticidal 5-pyrimidine carbonitriles |
-
1994
- 1994-07-14 SK SK103-96A patent/SK10396A3/sk unknown
- 1994-07-14 EP EP94923734A patent/EP0711285A1/en not_active Withdrawn
- 1994-07-14 CA CA002166989A patent/CA2166989A1/en not_active Abandoned
- 1994-07-14 AU AU73859/94A patent/AU7385994A/en not_active Abandoned
- 1994-07-14 BR BR9407024A patent/BR9407024A/pt not_active Application Discontinuation
- 1994-07-14 CZ CZ96224A patent/CZ22496A3/cs unknown
- 1994-07-14 JP JP7504913A patent/JPH09500632A/ja active Pending
- 1994-07-14 CN CN94192888.8A patent/CN1128024A/zh active Pending
- 1994-07-14 WO PCT/EP1994/002312 patent/WO1995003282A2/en not_active Ceased
- 1994-07-14 HU HU9503959A patent/HUT73357A/hu unknown
- 1994-07-25 IL IL11042594A patent/IL110425A0/xx unknown
-
1996
- 1996-01-24 FI FI960332A patent/FI960332A0/fi not_active Application Discontinuation
- 1996-01-25 NO NO960307A patent/NO960307L/no unknown
- 1996-02-19 BG BG100366A patent/BG100366A/xx unknown
- 1996-02-26 LV LVP-96-53A patent/LV11463B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO1995003282A3 (en) | 1995-04-13 |
| CN1128024A (zh) | 1996-07-31 |
| JPH09500632A (ja) | 1997-01-21 |
| CZ22496A3 (en) | 1996-04-17 |
| NO960307D0 (no) | 1996-01-25 |
| FI960332A7 (fi) | 1996-01-24 |
| HUT73357A (en) | 1996-07-29 |
| WO1995003282A2 (en) | 1995-02-02 |
| CA2166989A1 (en) | 1995-02-02 |
| EP0711285A1 (en) | 1996-05-15 |
| SK10396A3 (en) | 1996-09-04 |
| BR9407024A (pt) | 1996-09-10 |
| BG100366A (en) | 1996-07-31 |
| AU7385994A (en) | 1995-02-20 |
| IL110425A0 (en) | 1994-10-21 |
| HU9503959D0 (en) | 1996-03-28 |
| LV11463A (lv) | 1996-08-20 |
| NO960307L (no) | 1996-01-25 |
| FI960332A0 (fi) | 1996-01-24 |
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