HRP20130324T1 - Piridil-triazolopirimidin derivat ili njegove soli, pesticid koji ga sadržava i njegov proizvodni postupak - Google Patents
Piridil-triazolopirimidin derivat ili njegove soli, pesticid koji ga sadržava i njegov proizvodni postupak Download PDFInfo
- Publication number
- HRP20130324T1 HRP20130324T1 HRP20130324AT HRP20130324T HRP20130324T1 HR P20130324 T1 HRP20130324 T1 HR P20130324T1 HR P20130324A T HRP20130324A T HR P20130324AT HR P20130324 T HRP20130324 T HR P20130324T HR P20130324 T1 HRP20130324 T1 HR P20130324T1
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- Croatia
- Prior art keywords
- alkyl
- substituted
- formula
- image
- alkynyl
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims 9
- 238000004519 manufacturing process Methods 0.000 title claims 4
- 239000000575 pesticide Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 33
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000003342 alkenyl group Chemical group 0.000 claims 16
- 125000000304 alkynyl group Chemical group 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 125000001188 haloalkyl group Chemical group 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- -1 OR2 Inorganic materials 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 150000002576 ketones Chemical class 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 230000005494 condensation Effects 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- RDHMBEKEDDDWOF-UHFFFAOYSA-N 1h-[1,2,4]triazolo[1,5-a]pyrimidin-5-one Chemical class O=C1C=CN2NC=NC2=N1 RDHMBEKEDDDWOF-UHFFFAOYSA-N 0.000 claims 1
- 239000000642 acaricide Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 239000002917 insecticide Substances 0.000 claims 1
- 239000012434 nucleophilic reagent Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
Classifications
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Claims (8)
1. Piridil-triazolopirimidin derivat predstavljen formulom (I) ili njegove soli,
[image]
naznačen time, da je R1 alkil koji može biti supstituiran sa A, cikloalkil koji može biti supstituiran sa A, alkenil koji može biti supstituiran sa A, alkinil koji može biti supstituiran sa A, halogen, cijano, aril, heterociklička skupina, OR2, S(O)nR3, NR4R5;
R2 je vodik, alkil, alkenil, alkinil, haloalkil ili aril;
R3 je alkil;
R4 je vodik ili alkil;
R5 je vodik ili alkil;
A je halogen, OR2, S(O)nR3, NR4R5, cijano, cikloalkil, aril ili heterociklička skupina;
X je alkil, alkenil, alkinil, halogen, haloalkil, cijano ili nitro;
m je cijeli broj 1-4, i
n je cijeli broj 0-2.
2. Piridil-triazolopirimidin derivat ili njegova sol prema zahtjevu 1, naznačen time, da je R1 alkil, haloalkil, cikloalkil, alkenil, alkinil, cijano, aril, heterociklička skupina, OR2, S(O)nR3, NR4R5.
3. Piridil-triazolopirimidin derivat ili njegova sol prema zahtjevu 2, naznačen time, da je R1 alkil, haloalkil, cikloalkil ili alkenil.
4. Piridil-triazolopirimidin derivat ili njegova sol prema zahtjevu 1, naznačen time, da je R1 alkil, haloalkil, alkinil, cijano, aril, heterociklička skupina, OR2, S(O)nR3 ili NR4R5.
5. Insekticid ili miticid koji sadržava piridil-triazolopirimidin derivat ili njegovu sol kao što je definirano u zahtjevu 1, naznačen time, da je takav spoj aktivni sastojak.
6. Postupak za proizvodnju piridil-triazolopirimidin derivata predstavljen formulom (I) ili njegove soli,
[image]
naznačen time, da je R1 alkil koji može biti supstituiran sa A, cikloalkil koji može biti supstituiran sa A, alkenil koji može biti supstituiran sa A, alkinil koji može biti supstituiran sa A, halogen, cijano, aril, heterociklička skupina, OR2, S(O)nR3, NR4R5;
R2 je vodik, alkil, alkenil, alkinil, haloalkil ili aril;
R3 je alkil;
R4 je vodik ili alkil;
R5 je vodik ili alkil;
A je halogen, OR2, S(O)nR3, NR4R5, cijano, cikloalkil, aril, ili heterociklička skupina;
X je alkil, alkenil, alkinil, halogen, haloalkil, cijano, ili nitro;
m je cijeli broj 1-4, i
n je cijeli broj od 0 do 2, koji uključuje
(1) kondenziranje a, p-nezasićenog derivata ketona predstavljenog formulom (IV):
[image]
pri čemu su X i m kao što je definirano gore,
R1a je alkil koji može biti supstituiran sa A, cikloalkil koji može biti supstituiran sa A, alkenil koji može biti supstituiran sa A, alkinil koji može biti supstituiran sa A, arilom ili heterocikličkom skupinom, a R7 je alkil, i spoj predstavljen formulom (V):
[image]
(2) kondenziranje α,β-nezasićenog derivata ketona predstavljenog formulom (VII):
[image]
pri čemu su R3, X i m kao što je definirano gore, a spoj sa gore navedenom formulom (V);
[image]
(3) oksidiranje spoja prikazan formulom (I-2):
[image]
pri čemu su R3, X i m kao što je definirano gore,
(4) reakcija spoja prikazanog formulom (I-3):
[image]
pri čemu su R3, X i m kao što je definirano gore, a na je cijeli broj od 1-2, s nukleofilnim reagensom;
(5) kondenziranje spoja prikazanog formulom (IX):
[image]
gdje su X i m kao što je definirano gore, R1c je alkil koji može biti supstituiran sa A, cikloalkil koji može biti supstituiran sa A, alkenil koji može biti supstituiran sa A, alkinil koji može biti supstituiran sa A, aril ili heterociklička skupina i spoj prema gornjoj formuli (V); ili
(6) halogeniranje 4,5-dihidro-5-okso [1,2,4] triazolo [1,5-a] derivat pirimidina predstavljenog formulom (XV):
[image]
Gdje su X i m kao što je definirano gore.
7. Postupak za proizvodnju piridil-triazolopirimidin derivata predstavljen formulom (I-1), ili njegova sol,
[image]
naznačen time, da je R1a alkil koji može biti supstituiran sa A, cikloalkil koji može biti supstituiran sa A, alkenil koji može biti supstituiran sa A, alkinil koji može biti supstituiran sa A, arilom ili heterocikličkom skupinom; X je alkil, alkenil, alkinil, halogen, haloalkil, cijano, ili nitro;
R2 je vodik, alkil, alkenil, alkinil, haloalkil ili aril;
R3 je alkil;
R4 je vodik ili alkil;
R5 je vodik ili alkil;
A je halogen, OR2, S(O)nR3, NR4R5, cijano, cikloalkil, aril ili heterociklička skupina;
m je cijeli broj od 1-4, i
n je cijeli broj od 0-2;
koja obuhvaća kondenzaciju spoja prikazanog formulom (II):
[image]
gdje su X i m kao što je definirano gore, i spoj predstavljen formulom (III):
[image]
gdje je R1a definiran kao gore;
a svaki od R6 i R7, koji su neovisni jedan o drugome, je alkil, da se dobije α, β-nezasićeni derivat ketona predstavljen formulom (IV):
[image]
gdje su R1a, R7, X i m kao što je definirano gore, i kondenzaciju dobivenog derivata ketona i spoja predstavljenog formulom (V):
[image]
8. Postupak za proizvodnju piridil-triazolopirimidina derivata predstavljenog formulom (I-5) ili njegove soli,
[image]
naznačen time, da je R1c alkil koji može biti supstituiran sa A, cikloalkil koji može biti supstituiran sa A, alkenil koji može biti supstituiran sa A, alkinil koji može biti supstituiran sa A, arilom ili heterocikličkom skupinom;
X je alkil, alkenil, alkinil, halogen, haloalkil, cijano ili nitro;
R2 je vodik, alkil, alkenil, alkinil, haloalkil ili aril;
R3 je alkil;
R4 je vodik ili alkil;
R5 je vodik ili alkil;
A je halogen, OR2, S(O)nR3, NR4R5, cijano, cikloalkil, aril, ili heterociklička skupina;
m je cijeli broj od 1-4, i
n je cijeli broj od 0-2, koji uključuje
(1) reakciju spoja prikazanog formulom (II):
[image]
gdje su X i m kao što je definirano gore, sa spojem prema formuli (VIII):
pri čemu je R1c definiran kao gore, a R8 je alkil, ili
(2) reakciju spoja prikazanog formulom (X):
[image]
gdje su X i m kao što je definirano gore, a R9 je alkil, sa spojem formule (XVI):
[image]
pri čemu je R1c definiran kao gore, da se dobije spoj predstavljen formulom (IX):
[image]
pri čemu je R1c, X i m kao što je definirano gore, i
(3) kondenziranje spoja iz gornje formule (IX) i spoja predstavljenog formulom (V):
[image]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007034371 | 2007-02-15 | ||
| PCT/JP2008/052475 WO2008099902A1 (en) | 2007-02-15 | 2008-02-07 | Pyridyl-triazolopyrimidine derivative or its salt, pesticide containing it and its production process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20130324T1 true HRP20130324T1 (hr) | 2013-05-31 |
Family
ID=39319691
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20130324AT HRP20130324T1 (hr) | 2007-02-15 | 2013-04-10 | Piridil-triazolopirimidin derivat ili njegove soli, pesticid koji ga sadržava i njegov proizvodni postupak |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US8124760B2 (hr) |
| EP (1) | EP2118113B1 (hr) |
| JP (1) | JP5231829B2 (hr) |
| KR (1) | KR20090119854A (hr) |
| CN (1) | CN101611037B (hr) |
| AR (1) | AR065352A1 (hr) |
| AU (1) | AU2008215426A1 (hr) |
| BR (1) | BRPI0808126B1 (hr) |
| CA (1) | CA2676736A1 (hr) |
| CL (1) | CL2008000494A1 (hr) |
| DK (1) | DK2118113T3 (hr) |
| EG (1) | EG25529A (hr) |
| ES (1) | ES2400574T3 (hr) |
| HR (1) | HRP20130324T1 (hr) |
| IL (1) | IL200416A0 (hr) |
| MA (1) | MA31163B1 (hr) |
| MX (1) | MX2009008772A (hr) |
| NZ (1) | NZ578803A (hr) |
| PL (1) | PL2118113T3 (hr) |
| PT (1) | PT2118113E (hr) |
| RS (1) | RS52789B (hr) |
| SI (1) | SI2118113T1 (hr) |
| TW (1) | TW200902535A (hr) |
| WO (1) | WO2008099902A1 (hr) |
| ZA (1) | ZA200905370B (hr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011504505A (ja) | 2007-11-21 | 2011-02-10 | デコード ジェネティクス イーエイチエフ | 肺および心血管障害を治療するためのビアリールｐｄｅ４抑制剤 |
| JP2010065026A (ja) * | 2008-08-13 | 2010-03-25 | Ishihara Sangyo Kaisha Ltd | ピリジル−トリアゾロピリミジン誘導体又はその塩、並びにそれらを含有する有害生物防除剤 |
| WO2010059836A1 (en) * | 2008-11-20 | 2010-05-27 | Decode Genetics Ehf | Substituted aza-bridged bicyclics for cardiovascular and cns disease |
| TW201029575A (en) | 2009-01-29 | 2010-08-16 | Ishihara Sangyo Kaisha | Triazolopyrimidine derivative or its salt, process for producing the same and pesticide containing the same |
| JP2011168582A (ja) * | 2010-01-21 | 2011-09-01 | Ishihara Sangyo Kaisha Ltd | トリアゾロピリジン誘導体又はその塩、それらの製造方法及びそれらを含有する有害生物防除剤 |
| RU2016124136A (ru) * | 2010-08-18 | 2018-12-03 | СЭМЬЮМЕД, ЭлЭлСи | Дикетоны и гидроксикетоны в качестве активатора сигнального пути катенина |
| JP5959537B2 (ja) | 2011-01-28 | 2016-08-02 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 置換ピリジニル−ピリミジン及び医薬としてのその使用 |
| KR101339572B1 (ko) * | 2011-09-05 | 2013-12-10 | 이정은 | 초미립자 약제 살포기용 첨가제 |
| BR112015020391B1 (pt) | 2013-02-22 | 2022-07-26 | Samumed, Llc | Gama-dicetonas como ativadoras da via de sinalização de wnt/beta-catenina |
| PT3206686T (pt) | 2014-08-20 | 2020-01-06 | Samumed Llc | Gama-dicetonas para o tratamento e prevenção de rugas e do envelhecimento da pele |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4209621A (en) | 1979-04-27 | 1980-06-24 | American Cyanamid Company | (Substituted-phenyl)-1,2,4-triazolo[4,3-a]-pyrimidines and (substituted-phenyl)-1,2,4-triazolo[1,5-a]pyrimidines |
| US4444774A (en) * | 1982-07-29 | 1984-04-24 | American Cyanamid Company | 7-Heteroaryl[1,2,4]triazolo[1,5-a]pyrimidines |
| US4562192A (en) | 1984-02-03 | 1985-12-31 | G. D. Searle & Co. | 6-Substituted-5-phenyltetrazolo[1,5-a][1,2,4]triazole[1,5-c]pyrimidines, and pharmaceutical compositions containing them |
| EP1307200A2 (en) * | 2000-06-30 | 2003-05-07 | Wyeth | Substituted-triazolopyrimidines as anticancer agents |
| WO2004082383A1 (en) * | 2003-03-17 | 2004-09-30 | Basf Aktiengesellschaft | Use of triazolopyrimidines for combating nematode diseases of plants |
-
2008
- 2008-02-05 JP JP2008025572A patent/JP5231829B2/ja not_active Expired - Fee Related
- 2008-02-07 ES ES08711309T patent/ES2400574T3/es active Active
- 2008-02-07 CA CA002676736A patent/CA2676736A1/en not_active Abandoned
- 2008-02-07 AU AU2008215426A patent/AU2008215426A1/en not_active Abandoned
- 2008-02-07 ZA ZA200905370A patent/ZA200905370B/xx unknown
- 2008-02-07 BR BRPI0808126A patent/BRPI0808126B1/pt not_active IP Right Cessation
- 2008-02-07 WO PCT/JP2008/052475 patent/WO2008099902A1/en active Application Filing
- 2008-02-07 EP EP08711309A patent/EP2118113B1/en active Active
- 2008-02-07 KR KR1020097016972A patent/KR20090119854A/ko not_active Application Discontinuation
- 2008-02-07 RS RS20130033A patent/RS52789B/en unknown
- 2008-02-07 PL PL08711309T patent/PL2118113T3/pl unknown
- 2008-02-07 NZ NZ578803A patent/NZ578803A/en not_active IP Right Cessation
- 2008-02-07 DK DK08711309.8T patent/DK2118113T3/da active
- 2008-02-07 MX MX2009008772A patent/MX2009008772A/es active IP Right Grant
- 2008-02-07 PT PT87113098T patent/PT2118113E/pt unknown
- 2008-02-07 SI SI200830935T patent/SI2118113T1/sl unknown
- 2008-02-07 CN CN2008800050569A patent/CN101611037B/zh not_active Expired - Fee Related
- 2008-02-07 US US12/526,520 patent/US8124760B2/en not_active Expired - Fee Related
- 2008-02-14 TW TW097105200A patent/TW200902535A/zh unknown
- 2008-02-14 AR ARP080100635A patent/AR065352A1/es not_active Application Discontinuation
- 2008-02-15 CL CL200800494A patent/CL2008000494A1/es unknown
-
2009
- 2009-08-04 MA MA32139A patent/MA31163B1/fr unknown
- 2009-08-12 EG EG2009081217A patent/EG25529A/xx active
- 2009-08-13 IL IL200416A patent/IL200416A0/en unknown
-
2013
- 2013-04-10 HR HRP20130324AT patent/HRP20130324T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SI2118113T1 (sl) | 2013-06-28 |
| CN101611037B (zh) | 2012-11-28 |
| NZ578803A (en) | 2011-11-25 |
| BRPI0808126A2 (pt) | 2014-09-16 |
| PL2118113T3 (pl) | 2013-06-28 |
| ZA200905370B (en) | 2010-10-27 |
| CL2008000494A1 (es) | 2008-06-27 |
| JP2008222707A (ja) | 2008-09-25 |
| PT2118113E (pt) | 2013-03-14 |
| US20100087452A1 (en) | 2010-04-08 |
| EG25529A (en) | 2012-02-06 |
| KR20090119854A (ko) | 2009-11-20 |
| CN101611037A (zh) | 2009-12-23 |
| ES2400574T3 (es) | 2013-04-10 |
| RS52789B (en) | 2013-10-31 |
| US8124760B2 (en) | 2012-02-28 |
| WO2008099902A1 (en) | 2008-08-21 |
| DK2118113T3 (da) | 2013-02-18 |
| EP2118113A1 (en) | 2009-11-18 |
| BRPI0808126B1 (pt) | 2016-12-27 |
| MA31163B1 (fr) | 2010-02-01 |
| CA2676736A1 (en) | 2008-08-21 |
| MX2009008772A (es) | 2009-08-25 |
| AU2008215426A1 (en) | 2008-08-21 |
| AR065352A1 (es) | 2009-06-03 |
| TW200902535A (en) | 2009-01-16 |
| JP5231829B2 (ja) | 2013-07-10 |
| IL200416A0 (en) | 2010-04-29 |
| EP2118113B1 (en) | 2013-01-30 |
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