WO1986001207A1 - Pyridopyrimidine derivatives and process for their preparation - Google Patents
Pyridopyrimidine derivatives and process for their preparation Download PDFInfo
- Publication number
- WO1986001207A1 WO1986001207A1 PCT/JP1985/000441 JP8500441W WO8601207A1 WO 1986001207 A1 WO1986001207 A1 WO 1986001207A1 JP 8500441 W JP8500441 W JP 8500441W WO 8601207 A1 WO8601207 A1 WO 8601207A1
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- WO
- WIPO (PCT)
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- group
- lower alkyl
- alkyl group
- hydrogen
- substituted
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Definitions
- the present invention relates to a novel pyridopyrimidine derivative useful as a herbicide and a method for producing the same.
- the present invention is based on (1)-general formula [I] ⁇ li 3
- R 7 represents hydrogen, a lower alkyl group, an aralkyl group, a lower alkoxycarbonyl group, an aralkyloxycarbonyl group or an acyl group.
- J, R 2 is hydrogen or a lower alkyl group]
- R 3 is hydrogen, a lower alkyl group, an aralkyl group, an aryl group, a hydroxyl-substituted lower alkyl group, a lower alkoxy-substituted lower alkyl group
- Lanoxy group-substituted lower alkyl groups j and? 4 are hydrogen, lower alkyl groups or aralkyl groups. The same applies hereinafter.
- a method for producing the novel pyridopyrimidine derivative includes:
- R represents an aralkyl group xylcarbonyl or an acyl group among R 7 .
- R represents an aralkyl group xylcarbonyl or an acyl group among R 7 .
- R represents an aralkyl group xylcarbonyl or an acyl group among R 7 .
- R represents an aralkyl group xylcarbonyl or an acyl group among R 7 .
- R 8 represents a halogen, an alkoxy group and by the group et chosen Ru group of the nitro group] 9 unsubstituted or by good phenyl group optionally j9 substituted methyl group or hydrogen. The same applies hereinafter. ).
- Limidine derivative and general formula [w]
- the substance of the present invention is represented by the general formula [I].
- the lower alkyl group of the “phenyl group optionally substituted with a lower alkyl group” for R ! a methyl group, an ethyl group, a propyl group, and isoprohi.
- A a n-butyl group, an isobutyl group, a sec-butyl group, a ⁇ -butyl group, etc., among which a methyl group and an ethyl group are preferred, and the number of substitution with a lower alkyl group is usually 1 or 3].
- the number of substitutions is one.
- the phenyl group which may be substituted is preferably? Examples thereof include a 5-tolyl group and a V-ethylphenyl group.
- R is a group represented by the formula ( ⁇ )
- R 5 and R 6 are the same as those described above as the lower alkyl group, and the phenyl-substituted methyl group is a pendyl group, a diphenylmethyl group, or the like.
- the R 5 and 'R e are bonded to ⁇ alkylene group having 4 3 ⁇ 4 stone ⁇ carbon, particularly preferably one carbon teaching is 5.
- R 7 where R! Is a group represented by one ⁇ [[pi!],
- the lower alkyl group can be exemplified those listed before, preferably a methyl group, E Ji group,
- the aralkyl group include a benzyl group, a diphenylmethyl group, and a triphenylmethyl group. Of these, a benzyl group is preferable, and the aralkyl group is a benzyl group.
- Examples include diphenylenetinole, quinolone, and di-phenylene, and ⁇ -chlorophenylmethyloxycarbonyl, among which benzyloxycarbonyl is preferred.
- the lower alkoxycarbonyl is preferably Ethoxycarbonyl group, ethoxycarbonyl Examples thereof include a nore group, a propoxycarbinole group, an isopropoxycarbonyl group, and a ptoxylcarbonyl group, and among them, the former two groups are preferable.
- examples of the acyl group of R 7 include a formyl group, an acetyl group, an aromatic acyl such as a pionyl group, an aromatic acyl such as benzoyl and toluoyl, and among them, formyl and penzyl are preferred.
- examples of the lower alkyl group represented by? 2 and? 3 include those listed above.
- examples of the aralkyl group represented by R3 include those represented by R7, and the aryl group represented by phenyl group and 0.
- a phenyl group is preferable.
- methoxethyl is preferable.
- 2-tetrahydryl is preferred.
- the substance of the present invention is represented by the general formula [IV] (however, specific examples of R i or 4 in the formula are the same as those described in the description of the present substance. The same applies to other compounds hereinafter).
- a limidinidine carboxylic acid amide derivative By reacting a limidinidine carboxylic acid amide derivative with a formylating agent in the presence of a base.
- the compound represented by the general formula [W] can be obtained by the method described in the present applicant's application and the application filed on the same date and entitled “New limidine derivative and its production method” or a method based on the method, and further described below. Reference example: Which method is used?
- Examples of the formylating agent include N, N'-dimethylformamide, N, N'-getylformamide, methyl orthoformate, ethyl ethyl formate, methyl formate, and ethyl formate.
- N, N'-dimethylformamide and methyl formate are preferred.
- Examples of the base used in the reaction include NaII, NaNH 2 , LiH ⁇ LiNH 2 , LiN iso-pr) 2 , t-BOK ⁇ MeONa3 ⁇ 4, among which ⁇ ⁇ and t-BuOK Ka is preferred.
- the above-described formylating agent is also used as a solvent. Therefore, it is not necessary to use another solvent, but it may be used.
- other solvents such as hexane, benzene, toluene, and xylene may be used, such as hydrocarbon solvents, athenole, tetrahydrofuran, dithioxane, and dimethinoresnorreoxide. it can.
- N is usually used in a molar amount of 1 to 20 times, preferably 1 to 10 times the molar amount of the compound of the formula [N], and the base is usually used in a molar amount of 1 to 3 times.
- the reaction is usually carried out at a temperature of 20 to 25 (3 ° C, preferably 8 to 150 ° C) for 0.5 to 10 hours, depending on other conditions.
- Purification and isolation of the target compound can be carried out by a conventional method as described in Examples below.
- a compound represented by the general formula [I- ⁇ ] according to the present invention Lidohi.
- the lymidine derivative can be produced by hydrocracking the bilimidine derivative represented by the general formula [I-II] according to the present invention.
- the aralkyl groups for Ri include those listed for R 7 . This method can also be applied to the case of penzinolexyl carboxy, among the aranolequinoleoxycanoleboninole groups of R 7 . 1 ⁇
- ⁇ ⁇ -carbon Raney—Ni, pd0, etc. can be used as a hydrocracking catalyst.
- the amount of the catalyst used is 0.01 to 1 times (molar ratio) the compound [I--:].
- the reaction solvent is usually methanol, ethanol, or iso.
- -Acetic acid Using a mixed solvent and dioxane, usually under normal pressure or 10 atm, preferably under normal pressure or 5 atm under hydrogen pressure, at a temperature of 0 to 200 ° C, preferably 2 ° C. Incubate at 800 ° for 0.5 hours for 10 hours. Purification and isolation of the target substance are performed by a conventional method.
- the pyridovirimidine derivative represented by the general formula [I-] according to the present invention can also be obtained by acid-decomposing the pyridobilimidine derivative represented by the general formula [I-IV].
- the formula [I-II] examples of the aralkyl carbonyl group and the acyl group represented by? Include those listed in? 7 .
- Examples of the acid used in this method include sulfuric acid, SCI (gas), Ox Br (gas), and the like. These acids are used in an amount of 1% for the compound of the formula [I- ⁇ ].
- Water 100-fold molar use, water, methanol, ethanol, dioxane, THF-pense, benzene, tonolenene, xylene, formic acid, acetic acid, pulp.
- the reaction is carried out in a solvent such as ononic acid at a temperature of 0 to 10 CTC, preferably 2 (3 to 5 CTC) for 0.5 to 10 hours. After the reaction, the desired product is purified and isolated by the method shown in the Examples.
- the pyridopyrimidine derivative represented by the general formula [IV] according to the present invention is a compound represented by the general formula [V].
- the compound can be produced by reacting a lidopyrimidine derivative with a compound represented by the general formula [I:].
- the pyridopyrimidine derivative of the general formula [V] can be produced in accordance with the method described in the present invention [Production invention. 1].
- R 8 is chlorine, odor mottle which halogen, main butoxy group, Puroho 0 Kin group, a lower alkoxy group such as Isopurobokishi group, methyl substituted by the a phenyl group which may optionally be nucleus-substituted by a two preparative port group Group, for example, specifically, a benzyl group, a J) -chlorophenylmethyl group, a p-methoxyphenylmethyl group or hydrogen, and preferably a benzyl group or hydrogen.
- a two preparative port group Group for example, specifically, a benzyl group, a J) -chlorophenylmethyl group, a p-methoxyphenylmethyl group or hydrogen, and preferably a benzyl group or hydrogen.
- examples of the compound represented by the general formula [M] include lower alkoxycarbonyl groups and aralkyloxycarbonyl groups listed as 7 .
- reaction solvent aromatic hydrocarbons such as benzene, toluene and xylene, and ethers such as dioxane can be used, and preferably ⁇ .
- the substance has excellent activity as a herbicide. That is, the present substance can be used as a paddy field and upland herbicide.
- the weeds targeted by herbicides are especially effective against paddy field weeds, tamagayari, scallops, fireflies, spatula, and other upland weeds such as paddy weeds, hie, mexispa, aobu and kogomekaari.
- the substance of the present invention alone or a mixture of the substance with a body, a surfactant, a dispersant, an auxiliary agent and the like is formulated into a wettable powder, an emulsion, a fine particle or a granule. Dilute to an appropriate concentration and spray or apply directly.
- Na-sodium sodium 240 (0% in oil, 6 dishes 0 I) was washed with hexane and suspended in iV-dimethylformamide (Di) 5 / ⁇ . Then, 2 - dimethyl Ryomi Bruno - N - Echiru - 4 - Mechiruhi 0 Li Mi di emissions - 5 - Karubonami de 1. 0 4 g of (5 mm o I) of the i solution ⁇ Q nd) was added, 1 5 The reaction was performed at 0 ° C for 1.5 hours. F is distilled off under reduced pressure and then water 0 was added and extracted with ethyl acetate.
- Example 2 ⁇ -ethyl-2- (1-hydroxyperidinyl) pyridine [4,5-d .] arsenide Li Mi Jin - 5 (O) - sign yield: 0 7% mp: 1 5 1 ⁇ 1 5 2 ° C infrared absorption spectrum (S ⁇ tablets; - 1) 1 0 5 5 1 0 2 2, 1 5 7 5
- Field soil was packed into porcelain pots with an inner diameter of 9 cm, and Aobu, Kogome and Ryari were sown. Immediately, 300 g of a wettable powder containing the specified compound per 1 are dispersed in 20 liters of water, and sprayed over the entire surface of the soil with a small sprayer from above the pot. After the treatment, the plants were placed in a greenhouse for one day and the herbicidal efficacy was examined.
- novel compounds of the present invention are useful as herbicides c
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59/163772 | 1984-08-06 | ||
JP59163772A JPS6143190A (ja) | 1984-08-06 | 1984-08-06 | ピリドピリミジン誘導体およびその製法 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1986001207A1 true WO1986001207A1 (en) | 1986-02-27 |
Family
ID=15780422
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1985/000441 WO1986001207A1 (en) | 1984-08-06 | 1985-08-06 | Pyridopyrimidine derivatives and process for their preparation |
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JP (1) | JPS6143190A (he) |
WO (1) | WO1986001207A1 (he) |
Cited By (28)
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---|---|---|---|---|
CN102399225A (zh) * | 2011-11-28 | 2012-04-04 | 江西师范大学 | 具有除草活性的3-含氟取代苯甲酰胺基-3,4-二氢-4-亚胺-5-甲硫基-7-乙硫基嘧啶并[4,5-d]嘧啶及其制备方法 |
CN102491977A (zh) * | 2011-11-28 | 2012-06-13 | 江西师范大学 | 具有除草活性的1-取代苯氧亚甲基-8-烷硫基-10-甲硫基嘧啶并[5,4-e]-1,2,三唑并[1,5-c]嘧啶及制备方法 |
WO2018140600A1 (en) * | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | Fused hetero-hetero bicyclic compounds and methods of use thereof |
US10111874B2 (en) | 2014-09-18 | 2018-10-30 | Araxes Pharma Llc | Combination therapies for treatment of cancer |
US10144724B2 (en) | 2015-07-22 | 2018-12-04 | Araxes Pharma Llc | Substituted quinazoline compounds and methods of use thereof |
US10246424B2 (en) | 2015-04-10 | 2019-04-02 | Araxes Pharma Llc | Substituted quinazoline compounds and methods of use thereof |
US10273207B2 (en) | 2013-03-15 | 2019-04-30 | Araxes Pharma Llc | Covalent inhibitors of kras G12C |
US10280172B2 (en) | 2016-09-29 | 2019-05-07 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
US10370386B2 (en) | 2013-10-10 | 2019-08-06 | Araxes Pharma Llc | Substituted quinolines as inhibitors of KRAS G12C |
US10377743B2 (en) | 2016-10-07 | 2019-08-13 | Araxes Pharma Llc | Inhibitors of RAS and methods of use thereof |
US10414757B2 (en) | 2015-11-16 | 2019-09-17 | Araxes Pharma Llc | 2-substituted quinazoline compounds comprising a substituted heterocyclic group and methods of use thereof |
US10428064B2 (en) | 2015-04-15 | 2019-10-01 | Araxes Pharma Llc | Fused-tricyclic inhibitors of KRAS and methods of use thereof |
CN110382483A (zh) * | 2017-01-26 | 2019-10-25 | 亚瑞克西斯制药公司 | 稠合的n-杂环化合物及其使用方法 |
US10646488B2 (en) | 2016-07-13 | 2020-05-12 | Araxes Pharma Llc | Conjugates of cereblon binding compounds and G12C mutant KRAS, HRAS or NRAS protein modulating compounds and methods of use thereof |
US10647703B2 (en) | 2015-09-28 | 2020-05-12 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
US10689356B2 (en) | 2015-09-28 | 2020-06-23 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
US10730867B2 (en) | 2015-09-28 | 2020-08-04 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
US10736897B2 (en) | 2017-05-25 | 2020-08-11 | Araxes Pharma Llc | Compounds and methods of use thereof for treatment of cancer |
US10745385B2 (en) | 2017-05-25 | 2020-08-18 | Araxes Pharma Llc | Covalent inhibitors of KRAS |
US10858343B2 (en) | 2015-09-28 | 2020-12-08 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
US10875842B2 (en) | 2015-09-28 | 2020-12-29 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
US10882847B2 (en) | 2015-09-28 | 2021-01-05 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
US10975071B2 (en) | 2015-09-28 | 2021-04-13 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
US11136308B2 (en) | 2017-01-26 | 2021-10-05 | Araxes Pharma Llc | Substituted quinazoline and quinazolinone compounds and methods of use thereof |
US11274093B2 (en) | 2017-01-26 | 2022-03-15 | Araxes Pharma Llc | Fused bicyclic benzoheteroaromatic compounds and methods of use thereof |
US11279689B2 (en) | 2017-01-26 | 2022-03-22 | Araxes Pharma Llc | 1-(3-(6-(3-hydroxynaphthalen-1-yl)benzofuran-2-yl)azetidin-1 yl)prop-2-en-1-one derivatives and similar compounds as KRAS G12C modulators for treating cancer |
US11358959B2 (en) | 2017-01-26 | 2022-06-14 | Araxes Pharma Llc | Benzothiophene and benzothiazole compounds and methods of use thereof |
US11639346B2 (en) | 2017-05-25 | 2023-05-02 | Araxes Pharma Llc | Quinazoline derivatives as modulators of mutant KRAS, HRAS or NRAS |
-
1984
- 1984-08-06 JP JP59163772A patent/JPS6143190A/ja active Granted
-
1985
- 1985-08-06 WO PCT/JP1985/000441 patent/WO1986001207A1/ja unknown
Non-Patent Citations (1)
Title |
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CHEMICAL ABSTRACTS, Vol. 70, 11667 (1969). * |
Cited By (38)
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CN102399225A (zh) * | 2011-11-28 | 2012-04-04 | 江西师范大学 | 具有除草活性的3-含氟取代苯甲酰胺基-3,4-二氢-4-亚胺-5-甲硫基-7-乙硫基嘧啶并[4,5-d]嘧啶及其制备方法 |
CN102491977A (zh) * | 2011-11-28 | 2012-06-13 | 江西师范大学 | 具有除草活性的1-取代苯氧亚甲基-8-烷硫基-10-甲硫基嘧啶并[5,4-e]-1,2,三唑并[1,5-c]嘧啶及制备方法 |
CN102491977B (zh) * | 2011-11-28 | 2014-06-11 | 江西师范大学 | 一类具有除草活性的多取代嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶及制备 |
CN102399225B (zh) * | 2011-11-28 | 2014-09-24 | 江西师范大学 | 一类具有除草活性的含氟取代嘧啶并[4,5-d]嘧啶及制备 |
US10919850B2 (en) | 2013-03-15 | 2021-02-16 | Araxes Pharma Llc | Covalent inhibitors of KRas G12C |
US10273207B2 (en) | 2013-03-15 | 2019-04-30 | Araxes Pharma Llc | Covalent inhibitors of kras G12C |
US10370386B2 (en) | 2013-10-10 | 2019-08-06 | Araxes Pharma Llc | Substituted quinolines as inhibitors of KRAS G12C |
US10111874B2 (en) | 2014-09-18 | 2018-10-30 | Araxes Pharma Llc | Combination therapies for treatment of cancer |
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US10414757B2 (en) | 2015-11-16 | 2019-09-17 | Araxes Pharma Llc | 2-substituted quinazoline compounds comprising a substituted heterocyclic group and methods of use thereof |
US10646488B2 (en) | 2016-07-13 | 2020-05-12 | Araxes Pharma Llc | Conjugates of cereblon binding compounds and G12C mutant KRAS, HRAS or NRAS protein modulating compounds and methods of use thereof |
US10723738B2 (en) | 2016-09-29 | 2020-07-28 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
US10280172B2 (en) | 2016-09-29 | 2019-05-07 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
US10377743B2 (en) | 2016-10-07 | 2019-08-13 | Araxes Pharma Llc | Inhibitors of RAS and methods of use thereof |
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US10736897B2 (en) | 2017-05-25 | 2020-08-11 | Araxes Pharma Llc | Compounds and methods of use thereof for treatment of cancer |
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Also Published As
Publication number | Publication date |
---|---|
JPS6143190A (ja) | 1986-03-01 |
JPH0339508B2 (he) | 1991-06-14 |
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