TWI667229B - ５－氟－４－亞胺基－３－（烷基／經取代烷基）－１－（芳基磺醯基）－３，４－二氫嘧啶－２（１ｈ）－酮及其製備方法（二） - Google Patents
５－氟－４－亞胺基－３－（烷基／經取代烷基）－１－（芳基磺醯基）－３，４－二氫嘧啶－２（１ｈ）－酮及其製備方法（二） Download PDFInfo
- Publication number
- TWI667229B TWI667229B TW103146560A TW103146560A TWI667229B TW I667229 B TWI667229 B TW I667229B TW 103146560 A TW103146560 A TW 103146560A TW 103146560 A TW103146560 A TW 103146560A TW I667229 B TWI667229 B TW I667229B
- Authority
- TW
- Taiwan
- Prior art keywords
- compound
- dmf
- formula
- group
- alkali metal
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title abstract description 6
- -1 alkali metal alkoxide Chemical class 0.000 claims abstract description 18
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 12
- 239000002168 alkylating agent Substances 0.000 claims abstract description 12
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 23
- 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 description 15
- 239000007864 aqueous solution Substances 0.000 claims description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 150000003613 toluenes Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 150000001350 alkyl halides Chemical group 0.000 claims description 3
- VACOTYNWGUNJNC-UHFFFAOYSA-N ethane;hydroiodide Chemical compound I.CC VACOTYNWGUNJNC-UHFFFAOYSA-N 0.000 claims description 3
- QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 claims description 2
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- PKAUVIXBZJUYRV-UHFFFAOYSA-N methane;hydroiodide Chemical compound C.I PKAUVIXBZJUYRV-UHFFFAOYSA-N 0.000 claims 2
- 239000013043 chemical agent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 12
- 239000011734 sodium Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 5
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FDYDGPMTLJGGMJ-UHFFFAOYSA-N 4-amino-1-(benzenesulfonyl)-5-fluoropyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1S(=O)(=O)C1=CC=CC=C1 FDYDGPMTLJGGMJ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- VMLIAWXGDKYYQB-UHFFFAOYSA-N 1-benzylsulfonyl-5-fluoro-4-imino-3-methylpyrimidin-2-one Chemical compound FC=1C(N(C(N(C=1)S(=O)(=O)CC1=CC=CC=C1)=O)C)=N VMLIAWXGDKYYQB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 0 *c(cc1)ccc1S(N(C=C(C(N1*)=N)F)C1=O)(=O)=O Chemical compound *c(cc1)ccc1S(N(C=C(C(N1*)=N)F)C1=O)(=O)=O 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005421 aryl sulfonamido group Chemical group 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- FTUPGSSCBDRYLQ-UHFFFAOYSA-N benzylsulfanium;chloride Chemical class [Cl-].[SH2+]CC1=CC=CC=C1 FTUPGSSCBDRYLQ-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 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
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 description 1
- 229960004413 flucytosine Drugs 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 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
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical class [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium 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
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- 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
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
- C07D333/10—Thiophene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361922572P | 2013-12-31 | 2013-12-31 | |
| US201361922582P | 2013-12-31 | 2013-12-31 | |
| US61/922,582 | 2013-12-31 | ||
| US61/922,572 | 2013-12-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201609670A TW201609670A (zh) | 2016-03-16 |
| TWI667229B true TWI667229B (zh) | 2019-08-01 |
Family
ID=53480979
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW103146560A TWI667229B (zh) | 2013-12-31 | 2014-12-31 | ５－氟－４－亞胺基－３－（烷基／經取代烷基）－１－（芳基磺醯基）－３，４－二氫嘧啶－２（１ｈ）－酮及其製備方法（二） |
| TW103146555A TWI722979B (zh) | 2013-12-31 | 2014-12-31 | 5-氟-4-亞胺基-3-(烷基/經取代烷基)-1-(芳基磺醯基)-3,4-二氫嘧啶-2(1h)-酮及其製備方法（一） |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW103146555A TWI722979B (zh) | 2013-12-31 | 2014-12-31 | 5-氟-4-亞胺基-3-(烷基/經取代烷基)-1-(芳基磺醯基)-3,4-二氫嘧啶-2(1h)-酮及其製備方法（一） |
Country Status (24)
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2638556C2 (ru) | 2012-12-28 | 2017-12-14 | Адама Мактешим Лтд. | Производные n-(замещенного)-5-фтор-4-имино-3-метил-2-оксо-3,4-дигидропиримидин-1(2н)-карбоксилата |
| RU2015131149A (ru) | 2012-12-28 | 2017-02-03 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | N-(замещенные)-5-фтор-4-имино-3-метил-2-оксо-3,4-дигидропиримидин-1(2н)-карбоксамидные производные |
| RU2644014C2 (ru) | 2012-12-31 | 2018-02-07 | Адама Мактешим Лтд. | Производные 3-алкил-5-фтор-4-замещенного-имино-3,4-дигидропиримидин-2(н)-она в качестве фунгицидов |
| PH12016501285B1 (en) | 2013-12-31 | 2022-06-17 | Adama Makhteshim Ltd | Synergistic fungicidal mixtures for fungal control in cereals |
| UA122200C2 (uk) | 2013-12-31 | 2020-10-12 | Адама Махтешім Лтд. | 5-фтор-4-іміно-3-(алкіл/заміщений алкіл)-1-(арилсульфоніл)-3,4-дигідропіримідин-2(1h)-он і способи його одержання |
| UY36964A (es) | 2015-10-27 | 2017-05-31 | Bayer Cropscience Ag | Combinaciones de principios activos que comprenden un derivado de (tio) carboxamida y un compuesto funguicida |
| JP6922271B2 (ja) * | 2016-03-11 | 2021-08-18 | 住友化学株式会社 | 植物病害防除組成物及び植物病害防除方法 |
| IL309708B1 (en) * | 2017-07-17 | 2025-10-01 | Adama Makhteshim Ltd | Polymorphs of 5-fluoro-4-imino-3-methyl-1-tosyl-4,3-dihydropyrimidin-2-one |
| JP7701266B2 (ja) * | 2018-11-05 | 2025-07-01 | アダマ・マクテシム・リミテッド | ５－フルオロ－４－イミノ－３－メチル－１－トシル－３，４－ジヒドロピリミジン－２－オンを含む混合物および組成物、ならびにそれらの使用方法 |
| UY38798A (es) | 2019-07-22 | 2021-02-26 | Adama Makhteshim Ltd | Combinaciones, mezclas y composiciones fungicidas y usos de las mismas |
| TWI808347B (zh) * | 2019-09-23 | 2023-07-11 | 以色列商亞當馬赫特希姆有限公司 | 用於製備5-氟-4-亞胺基-3-甲基-1-甲苯磺醯基-3,4-二氫嘧啶-2(1h)-酮及該化合物的衍生物之方法 |
| US20230104954A1 (en) * | 2020-03-09 | 2023-04-06 | Adama Makhteshim Ltd. | Process for preparing 5-fluoro-4-imino-3-methyl-1-(toluene-4-sulfonyl)-3,4-dihydro-1h-pyrimidin-2-one |
| CR20220610A (es) * | 2020-05-04 | 2023-01-10 | Adama Makhteshim Ltd | Mezclas y composiciones que comprenden 5-fluoro-4-imino-3-metil-1-tosil-3,4-dihidropirimidin-2-ona, y métodos de uso de las mismas |
| CR20230077A (es) | 2020-07-08 | 2023-07-26 | Adama Makhteshim Ltd | Mezclas fungicidas |
| CA3206570A1 (en) | 2021-01-27 | 2022-08-04 | Alexandra ROSENMUND | 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1 h)-one for controlling plant diseases |
| US20240237649A1 (en) | 2021-05-04 | 2024-07-18 | Adama Makhteshim Ltd. | Crystalline forms of 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2-one, and mixtures, compositions and methods of use thereof |
| AR127068A1 (es) | 2021-09-15 | 2023-12-13 | Adama Makhteshim Ltd | Procedimiento para preparar 5-fluoro-4-imino-3-metil-1(tolueno-4-sulfonil)-3,4-dihidro-1h-pirimidin-2-ona |
| IL315414A (en) | 2022-03-03 | 2024-11-01 | Adama Makhteshim Ltd | Combinations, mixtures and preparations of fungicides, and their uses |
| CA3257550A1 (en) | 2022-05-26 | 2023-11-30 | Adama Makhteshim Ltd. | FUNGICIDAL COMBINATIONS, MIXTURES AND COMPOSITIONS AND THEIR USES |
| WO2024028812A1 (en) | 2022-08-03 | 2024-02-08 | Adama Makhteshim Ltd. | 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1h)-one for fungicide-resistant fungus |
| CN120882310A (zh) | 2023-03-09 | 2025-10-31 | 安道麦马克西姆有限公司 | 杀真菌组合、混合物及组合物以及其用途 |
| AU2024236967A1 (en) | 2023-03-14 | 2025-09-25 | Adama Makhteshim Ltd. | Liquid compositions containing 5-(fluoro-4-imino-3-methyl)-1-tosyl-3,4 dihydropyrimidine-(1h)-one and derivatives thereof and a uv absorber |
| TW202444696A (zh) | 2023-03-23 | 2024-11-16 | 以色列商安道麥馬克西姆有限公司 | 用於製備5-氟-4-亞胺基-3-甲基-1-(甲苯-4-磺醯基)-3,4-二氫-1h-嘧啶-2-酮的方法 |
| AR133680A1 (es) | 2023-08-31 | 2025-10-22 | Adama Makhteshim Ltd | Combinaciones, mezclas y composiciones fungicidas y usos de las mismas |
| IL308593A (en) | 2023-11-15 | 2025-06-01 | Adama Makhteshim Ltd | Reducing environmental impact of fungicidal enhancement |
| WO2025114931A1 (en) | 2023-11-28 | 2025-06-05 | Adama Makhteshim Ltd. | Fungicidal combinations, mixtures and compositions and uses thereof |
| WO2025203024A1 (en) | 2024-03-26 | 2025-10-02 | Adama Makhteshim Ltd. | Process for preparing 5-fluoro-4-imino-3-methyl-1-(toluene-4-sulfonyl)-3,4-dihydro-1h-pyrimidin-2-one |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013025795A1 (en) * | 2011-08-17 | 2013-02-21 | Dow Agrosciences Llc | 5-fluoro-4-imino-3-(substituted)-3,4-dihydropyrimidin-2-(1h)-one derivatives |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3309359A (en) | 1965-10-22 | 1967-03-14 | Hoffmann La Roche | N-mono-acyl-5-fluorocytosine derivatives and process |
| US3368938A (en) | 1966-01-13 | 1968-02-13 | Hoffmann La Roche | Controlling fungi with 5-fluorocytosine |
| US3635977A (en) | 1969-11-03 | 1972-01-18 | American Cyanamid Co | Certain 6-trifluoromethylcytosines and thiocytosines their synthesis and their use in the synthesis of uracisls and thiouracil |
| US3868373A (en) | 1970-01-27 | 1975-02-25 | Hoffmann La Roche | 4-Amino-5-fluoro-2-tri(lower alkyl) silyloxypyrimidines |
| US4009272A (en) | 1971-10-23 | 1977-02-22 | Bayer Aktiengesellschaft | Penicillins |
| CH579057A5 (cg-RX-API-DMAC7.html) | 1973-09-07 | 1976-08-31 | Hoffmann La Roche | |
| JPS601793B2 (ja) | 1979-12-06 | 1985-01-17 | 松下電器産業株式会社 | カラ−テレビジョン受像機の画質改善装置 |
| FR2530636A1 (fr) | 1982-07-23 | 1984-01-27 | Rhone Poulenc Agrochimie | Nouveaux derives de la tetrahydro-2,3,6,7 5h-thiazolo (3,2-a) pyrimidine, leur preparation et leur utilisation comme herbicides |
| EP0139613A1 (de) | 1983-08-29 | 1985-05-02 | Ciba-Geigy Ag | N-(2-Nitrophenyl)-4-aminopyrimidin-Derivate, deren Herstellung und Verwendung |
| US4845081A (en) | 1984-10-18 | 1989-07-04 | University Of Florida | Aminomethyl derivatives of biologically active substances, and enhanced delivery thereof across topical membranes |
| EP0230922A2 (de) | 1986-01-21 | 1987-08-05 | Boehringer Ingelheim Kg | Verwendung von Peptiden zur Herstellung von Mitteln zur Behandlung von Coronarerkrankungen oder organischem Hirnsyndrom |
| EP0332579B1 (de) | 1988-03-09 | 1994-08-10 | Ciba-Geigy Ag | Mittel zum Schutz von Pflanzen gegen Krankheiten |
| DE3821711A1 (de) | 1988-06-28 | 1990-02-08 | Bayer Ag | Thiazolopyrimidin-derivate, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| US5118816A (en) * | 1990-12-26 | 1992-06-02 | American Cyanamid Company | 2-aryl-5-(trifluoromethyl)-2-pyrroline compounds useful in the manufacture of insecticidal, nematocidal and acaricidal arylpyrroles |
| JP3109012B2 (ja) | 1992-06-18 | 2000-11-13 | クミアイ化学工業株式会社 | チアゾロ［５，４−ｄ］ピリミジン誘導体及び農園芸用殺菌剤 |
| JP3217191B2 (ja) | 1992-07-16 | 2001-10-09 | ビーエーエスエフ アクチェンゲゼルシャフト | ヘテロ芳香族化合物およびこれを含有する植物保護剤 |
| BR9609613A (pt) | 1995-07-05 | 1999-05-25 | Du Pont | Composto composição fungicida e método de controle de doenças de plantas |
| WO1997033890A1 (en) | 1996-03-11 | 1997-09-18 | Novartis Ag | Pyrimidin-4-one derivatives as pesticide |
| HRP970239B1 (en) * | 1997-05-09 | 2004-04-30 | Inst Ru Er Bouekovic | Process for the preparation of sulfonyl-pyrimidine derivatives with antitumor activity |
| GT199900185A (es) | 1998-11-06 | 2001-04-18 | Novedosa pirimidin-4-enamina como fungicida. | |
| CA2425359A1 (en) | 2000-10-13 | 2002-04-18 | Shire Biochem Inc. | Dioxolane analogs for improved inter-cellular delivery |
| US7914799B2 (en) | 2001-08-27 | 2011-03-29 | Immunitor USA, Inc. | Anti-fungal composition |
| US20080269238A1 (en) | 2004-04-01 | 2008-10-30 | Takeda Pharmaceutical Company Limited | Thiazolopyrimidine Derivative |
| US20090163567A1 (en) | 2005-11-22 | 2009-06-25 | Ishihara Sangyo Kaisha, Ltd | Germicide composition for agricultural and gardening applications and method for controlling plant disease |
| US20080004253A1 (en) | 2006-06-30 | 2008-01-03 | Bryan James Branstetter | Thiazolopyrimidine modulators of TRPV1 |
| US20100029483A1 (en) | 2006-10-16 | 2010-02-04 | Rhodia Inc. | Agricultural adjuvant compositions, pesticide compositions, and methods for using such compositions |
| KR101119809B1 (ko) | 2006-10-20 | 2012-03-21 | 수미도모 메탈 인더스트리즈, 리미티드 | 화학 플랜트용 니켈재 |
| WO2008083465A1 (en) | 2007-01-08 | 2008-07-17 | University Health Network | Pyrimidine derivatives as anticancer agents |
| PT2252594E (pt) | 2008-01-22 | 2015-11-30 | Dow Agrosciences Llc | Derivados de 5-fluoro-pirimidina como fungicidas |
| BRPI0916930A2 (pt) | 2008-08-01 | 2015-07-28 | Dow Agrosciences Llc | Uso de 5-fluorocitosina como um fungicida. |
| US8278341B2 (en) | 2008-09-17 | 2012-10-02 | Sri International | Analogs of indole-3-carbinol and their use as agents against infection |
| HUE025349T2 (en) | 2009-01-23 | 2016-02-29 | Euro Celtique Sa | Hydroxamic acid derivatives |
| US9006259B2 (en) * | 2009-08-07 | 2015-04-14 | Dow Agrosciences Llc | N1-sulfonyl-5-fluoropyrimidinone derivatives |
| UA106889C2 (uk) | 2009-08-07 | 2014-10-27 | ДАУ АГРОСАЙЄНСІЗ ЕлЕлСі | Похідні n1-ацил-5-фторпіримідинону |
| WO2011017544A1 (en) | 2009-08-07 | 2011-02-10 | Dow Agrosciences Llc | 5-fluoro-2-oxopyrimidine- 1(2h)-carboxylate derivatives |
| UA112284C2 (uk) | 2009-08-07 | 2016-08-25 | ДАУ АГРОСАЙЄНСІЗ ЕлЕлСі | Похідні 5-фторпіримідинону |
| UA107671C2 (en) | 2009-08-07 | 2015-02-10 | Dow Agrosciences Llc | N1-substityted-5-fluoro-2-oxopyrimidinone-1(2h)-carboxamide derivatives |
| WO2011043876A1 (en) | 2009-10-07 | 2011-04-14 | Dow Agrosciences Llc | Synergistic fungicidal composition containing 5-fluorocytosine for fungal control in cereals |
| CN102946730B (zh) * | 2010-04-26 | 2015-02-04 | 陶氏益农公司 | N3-取代的-n1-磺酰基-5-氟嘧啶酮衍生物 |
| EP2917952B1 (en) | 2012-11-07 | 2016-04-13 | Toyota Jidosha Kabushiki Kaisha | Method for producing a catalyst for fuel cells |
| RU2015131149A (ru) | 2012-12-28 | 2017-02-03 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | N-(замещенные)-5-фтор-4-имино-3-метил-2-оксо-3,4-дигидропиримидин-1(2н)-карбоксамидные производные |
| RU2638556C2 (ru) | 2012-12-28 | 2017-12-14 | Адама Мактешим Лтд. | Производные n-(замещенного)-5-фтор-4-имино-3-метил-2-оксо-3,4-дигидропиримидин-1(2н)-карбоксилата |
| AU2013370470B2 (en) * | 2012-12-28 | 2018-05-10 | Adama Makhteshim Ltd. | 1-(substituted-benzoyl)-5-fluoro-4-imino-3-methyl-3,4-dihydropyrimidin-2(1H)-one derivatives |
| RU2644014C2 (ru) * | 2012-12-31 | 2018-02-07 | Адама Мактешим Лтд. | Производные 3-алкил-5-фтор-4-замещенного-имино-3,4-дигидропиримидин-2(н)-она в качестве фунгицидов |
| UA122200C2 (uk) | 2013-12-31 | 2020-10-12 | Адама Махтешім Лтд. | 5-фтор-4-іміно-3-(алкіл/заміщений алкіл)-1-(арилсульфоніл)-3,4-дигідропіримідин-2(1h)-он і способи його одержання |
| PH12016501285B1 (en) | 2013-12-31 | 2022-06-17 | Adama Makhteshim Ltd | Synergistic fungicidal mixtures for fungal control in cereals |
| MA41272A (fr) | 2014-12-23 | 2017-10-31 | Adama Makhteshim Ltd | 5-fluoro-4-imino-3-(alkyle/alkyle substitué)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one en tant que traitement des semences |
-
2014
- 2014-12-29 UA UAA201608339A patent/UA122200C2/uk unknown
- 2014-12-29 UA UAA201909738A patent/UA129860C2/uk unknown
- 2014-12-29 EP EP14875976.4A patent/EP3094632A4/en not_active Ceased
- 2014-12-29 MX MX2016008759A patent/MX392211B/es unknown
- 2014-12-29 CR CR20210172A patent/CR20210172A/es unknown
- 2014-12-29 EA EA201691351A patent/EA036389B1/ru not_active IP Right Cessation
- 2014-12-29 CN CN201911242098.0A patent/CN111217759A/zh active Pending
- 2014-12-29 CN CN201911357017.1A patent/CN111362881A/zh active Pending
- 2014-12-29 WO PCT/US2014/072569 patent/WO2015103144A1/en not_active Ceased
- 2014-12-29 SG SG11201605372QA patent/SG11201605372QA/en unknown
- 2014-12-29 AU AU2014373959A patent/AU2014373959B2/en active Active
- 2014-12-29 WO PCT/US2014/072566 patent/WO2015103142A1/en not_active Ceased
- 2014-12-29 EP EP21151090.4A patent/EP3862346A1/en active Pending
- 2014-12-29 EP EP14877285.8A patent/EP3097096A4/en not_active Ceased
- 2014-12-29 NZ NZ722438A patent/NZ722438A/en unknown
- 2014-12-29 US US14/584,347 patent/US20150183749A1/en not_active Abandoned
- 2014-12-29 CA CA2935594A patent/CA2935594C/en active Active
- 2014-12-29 NZ NZ722439A patent/NZ722439A/en unknown
- 2014-12-29 AP AP2016009342A patent/AP2016009342A0/en unknown
- 2014-12-29 CA CA2935601A patent/CA2935601C/en active Active
- 2014-12-29 CR CR20160343A patent/CR20160343A/es unknown
- 2014-12-29 US US14/584,368 patent/US20150183750A1/en not_active Abandoned
- 2014-12-29 SG SG11201605377VA patent/SG11201605377VA/en unknown
- 2014-12-29 JP JP2016543746A patent/JP6804297B2/ja active Active
- 2014-12-29 EP EP21151157.1A patent/EP3862347A1/en not_active Withdrawn
- 2014-12-29 EA EA201691353A patent/EA201691353A1/ru unknown
- 2014-12-29 CN CN201480076563.7A patent/CN106068268A/zh active Pending
- 2014-12-29 JP JP2016543735A patent/JP6585057B2/ja active Active
- 2014-12-29 CN CN201480076583.4A patent/CN106061972B/zh active Active
- 2014-12-29 PE PE2016000974A patent/PE20161174A1/es unknown
- 2014-12-29 MX MX2016008758A patent/MX375727B/es active IP Right Grant
- 2014-12-29 AU AU2014373961A patent/AU2014373961B2/en active Active
- 2014-12-30 BR BR102014033010-0A patent/BR102014033010B1/pt active IP Right Grant
- 2014-12-30 UY UY0001035942A patent/UY35942A/es not_active Application Discontinuation
- 2014-12-30 BR BR102014033037-2A patent/BR102014033037B1/pt active IP Right Grant
- 2014-12-30 UY UY0001035943A patent/UY35943A/es not_active Application Discontinuation
- 2014-12-31 TW TW103146560A patent/TWI667229B/zh active
- 2014-12-31 TW TW103146555A patent/TWI722979B/zh active
-
2016
- 2016-06-03 US US15/173,493 patent/US9850215B2/en active Active
- 2016-06-03 US US15/173,529 patent/US9840476B2/en active Active
- 2016-06-28 IL IL24651116A patent/IL246511B/en active IP Right Grant
- 2016-06-28 IL IL246512A patent/IL246512B/en active IP Right Grant
- 2016-06-29 NI NI201600094A patent/NI201600094A/es unknown
- 2016-06-29 CL CL2016001677A patent/CL2016001677A1/es unknown
- 2016-06-29 PH PH12016501284A patent/PH12016501284A1/en unknown
- 2016-06-29 DO DO2016000163A patent/DOP2016000163A/es unknown
- 2016-07-29 EC ECIEPI201664249A patent/ECSP16064249A/es unknown
-
2017
- 2017-11-15 US US15/813,562 patent/US20180072686A1/en not_active Abandoned
-
2019
- 2019-06-21 US US16/448,633 patent/US20190308941A1/en not_active Abandoned
- 2019-09-04 JP JP2019160781A patent/JP2019218396A/ja not_active Withdrawn
- 2019-09-26 IL IL269694A patent/IL269694B/en unknown
- 2019-09-27 US US16/585,239 patent/US20200024238A1/en not_active Abandoned
-
2020
- 2020-01-13 US US16/741,026 patent/US10919864B2/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013025795A1 (en) * | 2011-08-17 | 2013-02-21 | Dow Agrosciences Llc | 5-fluoro-4-imino-3-(substituted)-3,4-dihydropyrimidin-2-(1h)-one derivatives |
Non-Patent Citations (1)
| Title |
|---|
| D. R. Birari et al.,"Synthesis of Cytosine Derivatives and Study of their Alkylation under Mild Conditions", Organic Preparations and Procedures International, Vol.41, No.6, January 2009, pages 515-532. * |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI667229B (zh) | ５－氟－４－亞胺基－３－（烷基／經取代烷基）－１－（芳基磺醯基）－３，４－二氫嘧啶－２（１ｈ）－酮及其製備方法（二） | |
| TW201726648A (zh) | 製備４－（（６－（２－（２，４－二氟苯基）－１，１－二氟－２－羥基－３－（１ｈ－１，２，４－三唑－１－基）丙基）吡啶－３－基）氧基）苄腈之方法 | |
| BR112020001278A2 (pt) | processo aprimorado para preparar derivados de aminopirimidina | |
| WO2013014665A1 (en) | Intermediate compounds and process for the preparation of lurasidone and salts thereof | |
| KR20200110381A (ko) | 술펜트라존의 합성 방법 | |
| HK40057090A (en) | Processes for their preparation of 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)- 3,4-dihydropyrimidin-2(1h)-one | |
| HK40057089A (en) | Processes for the preparation of 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)- 3,4-dihydropyrimidin-2(1h)-one | |
| EA044105B1 (ru) | 5-фтор-4-имино-3-(алкил/замещенный алкил)-1-(арилсульфонил)-3,4-дигидропиримидин-2(1h)-он и способы их получения | |
| EP3870568A1 (en) | Process for the preparation of rilpivirine | |
| JP2001220382A (ja) | 選択的ｏ−アルキル化方法 |