HRP20181037T1 - Postupak za pripremu derivata 4,6-bis(ariloksi)pirimidina - Google Patents
Postupak za pripremu derivata 4,6-bis(ariloksi)pirimidina Download PDFInfo
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- HRP20181037T1 HRP20181037T1 HRP20181037TT HRP20181037T HRP20181037T1 HR P20181037 T1 HRP20181037 T1 HR P20181037T1 HR P20181037T T HRP20181037T T HR P20181037TT HR P20181037 T HRP20181037 T HR P20181037T HR P20181037 T1 HRP20181037 T1 HR P20181037T1
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- Prior art keywords
- process according
- compound
- alkyl
- halogen
- hydrogen
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- 125000004104 aryloxy group Chemical group 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 cyano, nitro, acetyl Chemical group 0.000 claims 19
- 238000000034 method Methods 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 239000012429 reaction media Substances 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 150000003512 tertiary amines Chemical class 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- UOLVJRQJDZMNDG-UHFFFAOYSA-N 1,4-diazabicyclo[2.1.1]hexane Chemical compound C1N2CN1CC2 UOLVJRQJDZMNDG-UHFFFAOYSA-N 0.000 claims 1
- ZKMZPXWMMSBLNO-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-one Chemical compound C1CC2C(=O)CN1CC2 ZKMZPXWMMSBLNO-UHFFFAOYSA-N 0.000 claims 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims 1
- IVLICPVPXWEGCA-UHFFFAOYSA-N 3-quinuclidinol Chemical compound C1C[C@@H]2C(O)C[N@]1CC2 IVLICPVPXWEGCA-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000005087 alkynylcarbonyl group Chemical group 0.000 claims 1
- 125000005133 alkynyloxy group Chemical group 0.000 claims 1
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000004983 dialkoxyalkyl group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 230000022244 formylation Effects 0.000 claims 1
- 238000006170 formylation reaction Methods 0.000 claims 1
- 125000000262 haloalkenyl group Chemical group 0.000 claims 1
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 1
- 125000004995 haloalkylthio group Chemical group 0.000 claims 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims 1
- 239000004312 hexamethylene tetramine Substances 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 1
- 230000011987 methylation Effects 0.000 claims 1
- 238000007069 methylation reaction Methods 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000005429 oxyalkyl group Chemical group 0.000 claims 1
- 125000005702 oxyalkylene group Chemical group 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 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
- C07D239/52—Two oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Liquid Crystal Substances (AREA)
Claims (15)
1. Postupak za pripremu spoja opće formule (I)
koji sadrži ili:
a) reakciju spoja opće formule (II)
s alkoholom opće formule R6-OH, ili njegovom soli,
i) u prisustvu između 0.05 i 40 mol % jednog ili više tercijarnih amina katalizatora; i
ii) upotrebom vode kao reakcijskog medija i pri čemu reakcijski medij sadrži manje od 10 tež./tež.% organskog otapala;
ili
b) reakciju spoja opće formule (III)
sa spojem opće formule (IV)
ili njegovom soli,
i) u prisustvu između 0.05 i 40 mol % jednog ili više tercijarnih amina katalizatora; i
ii) upotrebom vode kao reakcijskog medija i pri čemu reakcijski medij sadrži manje od 10 tež./tež.% organskog rastvarača;
gdje:
LG predstavlja odlazeću grupu;
R1, R2, R3 i R4 predstavljaju, međusobno nezavisno, vodik, halogen, cijano, nitro, alkilkarbonil, formil, alkoksikarbonil, aminokarbonil, alkilaminokarbonil, dialkilaminokarbonil ili izborno halogenom-supstituirani alkil, aril, alkoksi, alkiltio, alkilsulfinil ili alkilsulfonil;
R5 je vodik, halogen, cijano, nitro, alkilkarbonil, formil, alkoksikarbonil, aminokarbonil, alkilaminokarbonil, dialkilaminokarbonil ili izborno halogenom-supstituirani alkil, aril, alkoksi, alkiltio, alkilsulfinil ili alkilsulfonil, ili jedan od sljedećih radikala:
gdje * označava točku vezivanja za fenil radikal formule (I);
R6 je supstituirani ili nesupstituirani aril, ili supstituirani ili nesupstituirani heterociklil, ili njegova sol;
R7 je vodik, fluor, klor ili brom;
uz uvjet da su R6 i radikal:
međusobno različiti.
2. Postupak prema patentnom zahtjevu 1, naznačen time što je katalizator izabran od jednog ili više sljedećih spojeva: 1,4-diazabiciklo[2.2.2]oktan (DABCO), N-metil-pirolidin, N-metilpiperidin, N-metilmorfolin, heksametilentetramin, 1,4-diazabiciklo[2.1.1]heksan, hinuklidin, 3-hinuklidinol ili 3-hinuklidinon.
3. Postupak prema bilo kojem od patentnih zahtjeva 1 ili 2, naznačen time što R1, R2, R3 i R4 su, nezavisno, vodik, fluor, klor, brom, cijano, nitro, acetil, propionil, metoksikarbonil, etoksikarbonil, aminokarbonil, metilaminokarbonil, etil-aminokarbonil, dimetilaminokarbonil, dietilaminokarbonil, metil, etil, n- ili i-propil, n-, i-, s- ili t-butil, metoksi, etoksi, n- ili i-propoksi, metiltio, etiltio, metilsulfinil, etilsulfinil, metilsulfonil, etilsulfonil, trifluorometil, trifluoroetil, difluorometoksi, trifluorometoksi, difluoroklorometoksi, trifluoroetoksi, difluorometiltio, difluoroklorometiltio, trifluorometiltio, trifluorometilsulfinil ili trifluorometilsulfonil.
4. Postupak prema patentnom zahtjevu 3, naznačen time što su R1, R2, R3 i R4, nezavisno, vodik ili metil.
5. Postupak prema patentnom zahtjevu 3 i 4, naznačen time što su R1, R2, R3 i R4 svaki vodik.
6. Postupak prema patentnom zahtjevu 1, naznačen time što R5 predstavlja jedan od sljedećih radikala:
ili njihovu smjesu, gdje * označava točku vezivanja za fenil radikal.
7. Postupak prema patentnom zahtjevu 6, naznačen time što R5 predstavlja jedan od sljedećih radikala:
ili
ili
ili
ili njihovu smjesu, gdje * označava točku vezivanja za fenil radikal.
8. Postupak prema patentnom zahtjevu 1, naznačen time što R6 predstavlja jedan od sljedećih:
heterociklus koji ima 3 do 7 članova prstena, izborno supstituran s halogenom ili sa C1-6 alkilom, C1-6 alkoksi, C1-6 halogenoalkilom ili C1-6 halogenoalkoksi; ili
fenil ili naftil, od koji je svaki izborno mono- do pentasupstituiran s identičnim ili različitim supstituentima izabranim iz grupe koja sadrži:
a. halogen, cijano, formil ili acetalom zaštićeni formil (na primjer dimetil ili dietil acetal, 1,3-dioksolan-2-il, 1,3-dioksan-2-il) karboksil, karbamoil, tiokarbamoil, aminokarbonil;
b. C1-8, ravnolančani ili razgranati, alkil, oksialkil, alkoksi, alkoksialkil, alkil-tioalkil, dialkoksialkil, alkiltio, alkilsufinil ili alkilsulfonil koji ima u svakom slučaju 1 do 8 atoma ugljika;
c. C2-6, ravnolančani ili razgranati, alkenil ili alkeniloksi;
d. C1-6, ravnolančani ili razgranati, halogenoalkil, halogenoalkoksi, halogeno-alkiltio, halogenoalkilsulfinil ili halogenoalkilsulfonil s između 1 i 13 identičnih ili različitih atoma halogena;
e. C2-6, ravnolančani ili razgranati, halogenoalkenil ili halogenoalkeniloksi s između 1 i 11 identičnih ili različitih atoma halogena;
f. C1-6, ravnolančani ili razgranati, dialkilamino, alkilkarbonil, alkilkarboniloksi, alkoksikarbonil, alkilaminokarbonil, dialkilaminokarbonil, arilalkil-aminokarbonil, dialkilaminokarboniloksi, alkenilkarbonil ili alkinilkarbonil;
g. C3-6 cikloalkil ili cikloalkiloksi;
h. dvostruko vezani C3-4 alkilen, C2-3 oksialkilen ili C1-2 dioksialkilen, od kojih je svaki izborno mono- do tetrasupstituiran s identičnim ili različitim supstituentima izabranim iz grupe koja se sastoji od fluora, klora, okso, metila, trifluorometila i etila; ili
i. radikal
u kojem:
R8 je vodik, hidroksil, C1-4 alkil ili C1-6 cikloalkil; i
R9 predstavlja hidroksil, metoksi, etoksi, amino, metilamino, fenil ili benzil; ili predstavlja C1-4 alkil ili alkoksi, izborno supstituiran s cijano-, alkoksi-, alkiltio-, alkilamino-, dialkilamino- ili fenil; ili predstavlja C2-4 alkeniloksi ili alkinilioksi; ili predstavlja benzoil, benzoiletenil, cinamoil, heterociklil; ili predstavlja fenilalkil, fenilalkiloksi ili heterociklilalkil, koji ima u svakom slučaju 1 do 3 atoma ugljika u alkil grupama i koji je u svakom slučaju izborno mono- do trisupstituiran u grupi prstena s halogenom i/ili ravnolančanim ili razgranatim C1-4 alkilom ili alkoksi.
9. Postupak prema patentnom zahtjevu 8, naznačen time što je R6 2-cijanofenil.
10. Postupak prema patentnom zahtjevu 1, naznačen time što je R7 vodik, fluor ili klor.
11. Postupak prema patentnom zahtjevu 1 za pripremu spoja formule (Ia)
12. Postupak prema patentnom zahtjevu 1 za pripremu spoja formule (Ib)
13. Postupak prema patentnom zahtjevu 1 za pripremu spoja formule (Id)
14. Postupak prema patentnom zahtjevu 13, naznačen time što je spoj formule (Id) dalje podvrgnut koraku formilacije praćen korakom metilacije da bi se dobilo spoj opće formule (If)
15. Postupak prema patentnom zahtjevu 14, naznačen time što postupak sadrži sljedeću reakcijsku sekvencu
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13169497 | 2013-05-28 | ||
| EP14729204.9A EP3004066B1 (en) | 2013-05-28 | 2014-05-27 | Process for preparing 4,6-bis(aryloxy)pyrimidine derivatives |
| PCT/DK2014/050145 WO2014190997A1 (en) | 2013-05-28 | 2014-05-27 | Process for preparing 4,6-bis(aryloxy)pyrimidine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20181037T1 true HRP20181037T1 (hr) | 2018-08-24 |
Family
ID=48482979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20181037TT HRP20181037T1 (hr) | 2013-05-28 | 2018-07-05 | Postupak za pripremu derivata 4,6-bis(ariloksi)pirimidina |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US9643935B2 (hr) |
| EP (1) | EP3004066B1 (hr) |
| CN (1) | CN105246878B (hr) |
| BR (1) | BR112015029714B1 (hr) |
| CY (1) | CY1120380T1 (hr) |
| DK (1) | DK3004066T3 (hr) |
| ES (1) | ES2675892T3 (hr) |
| HR (1) | HRP20181037T1 (hr) |
| HU (1) | HUE038326T2 (hr) |
| IL (1) | IL242460A (hr) |
| LT (1) | LT3004066T (hr) |
| MX (1) | MX2015016287A (hr) |
| PL (1) | PL3004066T3 (hr) |
| PT (1) | PT3004066T (hr) |
| RS (1) | RS57374B1 (hr) |
| SI (1) | SI3004066T1 (hr) |
| TR (1) | TR201809656T4 (hr) |
| TW (1) | TWI621614B (hr) |
| WO (1) | WO2014190997A1 (hr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106008367A (zh) * | 2015-11-20 | 2016-10-12 | 江苏长青农化股份有限公司 | 嘧菌酯合成方法 |
| CN109721548B (zh) * | 2017-10-31 | 2020-11-13 | 南通泰禾化工股份有限公司 | 一种嘧菌酯的制备方法 |
| CN109529928B (zh) * | 2018-11-16 | 2021-06-29 | 河北威远生物化工有限公司 | 一种催化剂体系及利用其制备嘧菌酯或其中间体的方法 |
| TWI705961B (zh) * | 2018-11-28 | 2020-10-01 | 興農股份有限公司 | 亞托敏的製備方法 |
| BR112021020906A2 (pt) * | 2019-04-18 | 2022-04-19 | Upl Ltd | Processo para a preparação de azoxistrobina e intermediários da mesma |
| CN118084805A (zh) * | 2022-05-26 | 2024-05-28 | 安徽广信农化股份有限公司 | 一种制备嘧菌酯及其中间体的方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3789683T2 (de) | 1986-04-17 | 1994-08-25 | Zeneca Ltd | Fungizide. |
| GB9122430D0 (en) | 1990-11-16 | 1991-12-04 | Ici Plc | Chemical process |
| GB9415291D0 (en) | 1994-07-28 | 1994-09-21 | Zeneca Ltd | Chemical process |
| US5977363A (en) * | 1996-03-07 | 1999-11-02 | American Cyanamid Company | Process for the preparation of unsymmetrical 4,6-bis(aryloxy) pyrimidine compounds |
| GB9617351D0 (en) | 1996-08-19 | 1996-10-02 | Zeneca Ltd | Chemical process |
| GB9622345D0 (en) | 1996-10-28 | 1997-01-08 | Zeneca Ltd | Chemical process |
| US5849910A (en) * | 1997-09-05 | 1998-12-15 | American Cyanamid Company | Process for the preparation of unsymmetrical 4,6-bis aryloxy-pyrimidine compounds |
| US6087498A (en) * | 1998-05-12 | 2000-07-11 | American Cyanamid Company | Process for the preparation of unsymmetrical 4,6-bis(aryloxy) pyrimidine compounds |
| DE10014607A1 (de) | 2000-03-24 | 2001-09-27 | Bayer Ag | Verfahren zur Herstellung von unsymmetrischen 4,6-Bis(aryloxy pyrimidin-Derivaten |
| GB0508422D0 (en) | 2005-04-26 | 2005-06-01 | Syngenta Ltd | Chemical process |
| GB0619942D0 (en) | 2006-10-09 | 2006-11-15 | Syngenta Ltd | Chemical process |
| GB0619941D0 (en) * | 2006-10-09 | 2006-11-15 | Syngenta Ltd | Chemical process |
| IL180134A0 (en) | 2006-12-17 | 2007-07-04 | David Ovadia | Process for the preparation of substituted cyanophenoxy-pyrimidinyloxy -phenyl acrylate derivatives |
| CN100564362C (zh) | 2007-10-24 | 2009-12-02 | 北京颖泰嘉和科技股份有限公司 | 嘧菌酯及其类似物的制备方法 |
| CN102399195A (zh) * | 2011-12-08 | 2012-04-04 | 北京颖新泰康国际贸易有限公司 | 一种嘧菌酯中间体的合成方法 |
-
2014
- 2014-05-07 TW TW103116247A patent/TWI621614B/zh active
- 2014-05-27 BR BR112015029714-5A patent/BR112015029714B1/pt active IP Right Grant
- 2014-05-27 HU HUE14729204A patent/HUE038326T2/hu unknown
- 2014-05-27 ES ES14729204.9T patent/ES2675892T3/es active Active
- 2014-05-27 TR TR2018/09656T patent/TR201809656T4/tr unknown
- 2014-05-27 RS RS20180733A patent/RS57374B1/sr unknown
- 2014-05-27 PT PT147292049T patent/PT3004066T/pt unknown
- 2014-05-27 PL PL14729204T patent/PL3004066T3/pl unknown
- 2014-05-27 MX MX2015016287A patent/MX2015016287A/es active IP Right Grant
- 2014-05-27 DK DK14729204.9T patent/DK3004066T3/en active
- 2014-05-27 EP EP14729204.9A patent/EP3004066B1/en active Active
- 2014-05-27 LT LTEP14729204.9T patent/LT3004066T/lt unknown
- 2014-05-27 WO PCT/DK2014/050145 patent/WO2014190997A1/en active Application Filing
- 2014-05-27 CN CN201480029478.5A patent/CN105246878B/zh active Active
- 2014-05-27 SI SI201430760T patent/SI3004066T1/en unknown
- 2014-05-27 US US14/893,666 patent/US9643935B2/en active Active
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2015
- 2015-11-04 IL IL242460A patent/IL242460A/en active IP Right Grant
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Also Published As
| Publication number | Publication date |
|---|---|
| TW201444802A (zh) | 2014-12-01 |
| CN105246878B (zh) | 2017-12-15 |
| PL3004066T3 (pl) | 2018-09-28 |
| CN105246878A (zh) | 2016-01-13 |
| CY1120380T1 (el) | 2019-07-10 |
| EP3004066B1 (en) | 2018-04-11 |
| TR201809656T4 (tr) | 2018-07-23 |
| HUE038326T2 (hu) | 2018-10-29 |
| US20160137612A1 (en) | 2016-05-19 |
| MX2015016287A (es) | 2016-03-11 |
| ES2675892T3 (es) | 2018-07-13 |
| DK3004066T3 (en) | 2018-06-14 |
| TWI621614B (zh) | 2018-04-21 |
| EP3004066A1 (en) | 2016-04-13 |
| SI3004066T1 (en) | 2018-08-31 |
| PT3004066T (pt) | 2018-07-16 |
| WO2014190997A1 (en) | 2014-12-04 |
| IL242460A (en) | 2017-10-31 |
| LT3004066T (lt) | 2018-07-10 |
| RS57374B1 (sr) | 2018-08-31 |
| US9643935B2 (en) | 2017-05-09 |
| BR112015029714B1 (pt) | 2020-12-15 |
| BR112015029714A2 (pt) | 2017-07-25 |
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