WO1986001207A1 - Derives de pyridopyrimidine et leur procede de preparation - Google Patents

Derives de pyridopyrimidine et leur procede de preparation Download PDF

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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)
Prior art keywords
group
lower alkyl
alkyl group
hydrogen
substituted
Prior art date
Application number
PCT/JP1985/000441
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English (en)
Japanese (ja)
Inventor
Noriaki Kihara
Tatsuyoshi Ishida
Shigeru Isayama
Takeshi Ishitoku
Hiroaki Tan
Katsuya Takahashi
Original Assignee
Mitsui Petrochemical Industries, Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mitsui Petrochemical Industries, Ltd. filed Critical Mitsui Petrochemical Industries, Ltd.
Publication of WO1986001207A1 publication Critical patent/WO1986001207A1/fr

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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

Abstract

Nouveaux composés de formule (I), où R1 représente un groupe phényle éventuellement substitué par un groupe alkyle inférieur, un groupe de formule (II) (où R5 et R6 représentent chacun H, un groupe alkyle inférieur, ou un groupe méthyle substitué par un groupe phényle, ou alors R5 et R6 représentent ensemble un groupe alkylène comportant de 4 à 6 C) ou un groupe de formule (III) (où n vaut 2 ou 3, R7 représente H, un groupe alkyle inférieur, un groupe aralkyle, un groupe alkoxycarbonyle inférieur, un groupe aralkyloxycarbonyle ou un groupe acyle); R2 représente H ou un groupe alkyle inférieur; R3 représente H, un groupe alkyle inférieur, un groupe aralkyle, un groupe aryle, un groupe alkyle inférieur substitué par un groupe hydroxyle, un groupe alkyle inférieur substitué par un groupe alkoxy inférieur ou un groupe alkyle inférieur substitué par un groupe tétrahydropyranoxy; R4 est H, un groupe alkyle inférieur ou un groupe aralkyle. Est également décrit un procédé de préparation de ces dérivés, utiles en tant qu'herbicides.
PCT/JP1985/000441 1984-08-06 1985-08-06 Derives de pyridopyrimidine et leur procede de preparation WO1986001207A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
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
JP59/163772 1984-08-06

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WO1986001207A1 true WO1986001207A1 (fr) 1986-02-27

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JP (1) JPS6143190A (fr)
WO (1) WO1986001207A1 (fr)

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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,***并[1,5-c]嘧啶及制备方法
WO2018140600A1 (fr) * 2017-01-26 2018-08-02 Araxes Pharma Llc Composés hétéro-hétéro-bicycliques fusionnés et leurs procédés d'utilisation
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

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* Cited by examiner, † Cited by third party
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Cited By (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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,***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-***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
US10246424B2 (en) 2015-04-10 2019-04-02 Araxes Pharma Llc Substituted quinazoline compounds and methods of use thereof
US10829458B2 (en) 2015-04-10 2020-11-10 Araxes Pharma Llc Substituted quinazoline compounds 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
US10144724B2 (en) 2015-07-22 2018-12-04 Araxes Pharma Llc Substituted quinazoline compounds and methods of use thereof
US10351550B2 (en) 2015-07-22 2019-07-16 Araxes Pharma Llc Substituted quinazoline compounds and methods of use thereof
US10882847B2 (en) 2015-09-28 2021-01-05 Araxes Pharma Llc Inhibitors of KRAS G12C mutant proteins
US10858343B2 (en) 2015-09-28 2020-12-08 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
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
US10875842B2 (en) 2015-09-28 2020-12-29 Araxes Pharma Llc Inhibitors of KRAS G12C mutant proteins
US11021470B2 (en) 2015-11-16 2021-06-01 Araxes Pharma Llc 2-substituted quinazoline compounds comprising a substituted heterocyclic group 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
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
CN110382482A (zh) * 2017-01-26 2019-10-25 亚瑞克西斯制药公司 稠合的杂-杂二环化合物及其使用方法
WO2018140600A1 (fr) * 2017-01-26 2018-08-02 Araxes Pharma Llc Composés hétéro-hétéro-bicycliques fusionnés et leurs procédés d'utilisation
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
US11059819B2 (en) 2017-01-26 2021-07-13 Janssen Biotech, Inc. Fused hetero-hetero bicyclic compounds and methods of use thereof
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
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
US11377441B2 (en) 2017-05-25 2022-07-05 Araxes Pharma Llc Covalent inhibitors of KRAS
US11639346B2 (en) 2017-05-25 2023-05-02 Araxes Pharma Llc Quinazoline derivatives as modulators of mutant KRAS, HRAS or NRAS

Also Published As

Publication number Publication date
JPH0339508B2 (fr) 1991-06-14
JPS6143190A (ja) 1986-03-01

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