JPH03178966A - Production of 1-isoquinolines - Google Patents
Production of 1-isoquinolinesInfo
- Publication number
- JPH03178966A JPH03178966A JP1318488A JP31848889A JPH03178966A JP H03178966 A JPH03178966 A JP H03178966A JP 1318488 A JP1318488 A JP 1318488A JP 31848889 A JP31848889 A JP 31848889A JP H03178966 A JPH03178966 A JP H03178966A
- Authority
- JP
- Japan
- Prior art keywords
- raw material
- alcohol
- chloride
- formula
- palladium
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 8
- 229910021591 Copper(I) chloride Inorganic materials 0.000 abstract description 6
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 abstract description 6
- 229940045803 cuprous chloride Drugs 0.000 abstract description 6
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 abstract description 6
- 239000003054 catalyst Substances 0.000 abstract description 5
- CWIAYCPUWVIULX-UHFFFAOYSA-N 2-ethenylbenzamide Chemical compound NC(=O)C1=CC=CC=C1C=C CWIAYCPUWVIULX-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 abstract description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract description 2
- 239000005977 Ethylene Substances 0.000 abstract description 2
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 229930013930 alkaloid Natural products 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 abstract description 2
- 238000007363 ring formation reaction Methods 0.000 abstract description 2
- NHNAEZDWNCRWRW-UHFFFAOYSA-N 2-bromobenzamide Chemical compound NC(=O)C1=CC=CC=C1Br NHNAEZDWNCRWRW-UHFFFAOYSA-N 0.000 abstract 1
- 150000003797 alkaloid derivatives Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 150000002537 isoquinolines Chemical class 0.000 description 2
- -1 olefin compound Chemical class 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- VECCBMBUQUFSPO-UHFFFAOYSA-N 2-ethynylbenzamide Chemical class NC(=O)C1=CC=CC=C1C#C VECCBMBUQUFSPO-UHFFFAOYSA-N 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000007333 cyanation reaction Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Abstract
Description
本発明は、２−エチニルベンズアミド類を出発原料とす
る１−イソキノリン類の製造方法に関するものである。
１−イソキノリン類は、染料、香料、医薬、農薬などの
分野において広範囲に使用されている物質であり、特に
アルカロイドの合成原料として有用性の高いものである
。The present invention relates to a method for producing 1-isoquinolines using 2-ethynylbenzamides as a starting material. 1-isoquinolines are substances that are widely used in the fields of dyes, fragrances, medicines, agricultural chemicals, etc., and are particularly useful as raw materials for the synthesis of alkaloids.
１−イソキノリン類の合成法としては、古くがら数−）
くのＪｊ法か研究さズしてきて」、す、代表的なｈ−法
どし７ては、イソキノリンとアシモニアとの反応、イソ
キノリンの酸化、］−］アミーノイソキノリのシアン化
なとか知られているか、それぞれに長所、短所を有して
おり、１−イソキノリ〉類の工業的な製法としては）１
′４足のいくものではなかった。As a method for synthesizing 1-isoquinolines, the traditional method is number-)
I have been researching many Jj methods, and I know of some typical H-methods, such as the reaction between isoquinoline and asimonia, the oxidation of isoquinoline, and the cyanation of ]-]aminoisoquinol. Each method has its advantages and disadvantages, and the industrial manufacturing methods for 1-isoquinolites are 1)
'It wasn't something I could do with four legs.
【発明か解決し、［うとする課題］
本発明の目的は、特に１−、イソキノリン環の５−８位
に直換基を有する］−イソキノリ＞類を、温和な条件で
島純度かつ好酸４．−て製造する方法を・提供すること
である。
【課題を解決づ−るための手段】
ずなわち、本発明は、一般式＜Ｉ）
素原子、フン素原子、塩素原子、炭素数１−・−３のア
ルキノ１基、炭素数１〜３のアルコキシ基、二）〜口方
−および゛シアルＡ−ルアミノスルホニル基から選はれ
る１種の基を表す〕
て示される２−ニブニルベンズアミ１〜類を塩化パラジ
ウムと塩１ヒ第−銅およびアルコールの存在下、酸素雰
囲気中て反応させることを特徴とする−・般式（Ｈ）
〔式中、’Ｒ１，Ｆ？、２ 、 Ｒ３、Ｒ，４は前記定
義に同し〕
で示される］−イソキノリン類の製造方法に関するもの
である。
本発明により得られる１−インキノリン類は、未置換の
１−イソキノリンおよびヘンセン環に置換基をイｊケる
コーイソキノリン［Ｌき物である。置換基（は、フッ素
原子、塩素原子、炭素数１〜３のアルキル基、炭素数１
〜３のアルコキシ基、二１ヘロ基およびジアルキルアミ
ノスルホニル基て、５−８位のいずれかの位置に少なく
とも１つ置換さ！したものである、
本発明により摺Ｉ；れるコーイソキノリン類を具体的に
示せは、１−イソキノリ〉′、６−フロロ１ イソキノ
リン、５−クロロ−１−イソキノリン、７−クロロ−１
−イソキノリ〉、５−メチル］−インキノリン、６−メ
チル＝−１−イソキノノン、７−メチル−１−イソキノ
リン、８−メチル−１−イソキノリン、６−メ１ヘキシ
−１−イソキノノン、７−メ１〜キシ−１−イソキノリ
ン、６二１−ロー ｊ−イソキノリンおよび６−シメチ
ルアミノスルポニルー１−イソキノリンなどが挙げられ
る。
本発明の出発原」ミ［となる前記＝・般式（Ｉ）て示さ
れる２−エテニルヘンズアミド類は、２−フロ１８ベン
スアミ１へ類に酢酸パラジウム触媒の存在下エチレンカ
スを反応させることにより容易に製造することかてきる
（ Ｒ，Ｆ、Ｈｅｃｋ、 Ｏｒｇ、Ｒｅａｃｔ、 、
２７３４．５．（］、９８２） ） 。
本発明は、２−エテニルベンスアミド類に塩化パラジウ
ｊ＼、塩化第一銅およびアルコールの存在下、酸素雰囲
気中で環化反応させて、−・般式（ＩＩ）の１−インキ
ノリン類を製造する方法である。
オレフィン化合物をパラジウム錯体触媒を用いて酸化を
行いカルボニル化合物を祠る反応は、殻間にワ・ツカ−
反応として知られているか、スチレン誘導体のワラカー
反応てはアセ１〜フヱノン誘導体かｌｔ’Ａられるのが
通例である。木・発明者らは、パラジウム錯体触媒にス
チレン誘導体の酸化反応の研究を鋭意進めた結果、塩化
第一銅を助触媒としてアルコールの存在下、酸素雰囲気
中で２−エチニルへ〉′ズアミト類がパラジウム触媒に
よって１−イソキノリン類に効率的に変換できることを
見いたし、本発明を完成させるに至ったものである。
本発明方法において用いられるアルコールとしては、メ
タノーノし、エタノール、プロパツール、フタノールな
との低級アル−７−ルＪ３よひニーｊし〉クリコール、
］、３−プ）コバ＞５オールなとのタフコール類のいず
れてもよい３
本発明の反Ｌｅ２条１′１は、胤（ヒノヘ゛ラシｆ７）
・（、ｌ原料に名１し２て１−１００モル０゜、塩ｆヒ
第一・相は１−２倍モルｆ重用３−ろσ）か−Ｌい ア
ルニア −ＩＬ、は、二２−エテニルヘンズアミト類の
］〜１−１５モル使用するのか好よしく、溶媒と１−で
はジオ”−リーン、テｌ−ラヒＩ・ロフラ＞、 １．
、２−シメトキシエタシなとか好適て゛あっる。
本発明の反応は、はぼ常圧のＫ 木含有のζｒ在下、・
１０〜８０℃に加熱撹拌することにより容易に進行する
。反応最は、再結晶よ／ｉ：はカラムクロマ１−クラフ
ィーといった一般的な精製手段て、１イソキノリシ１ｆ
１を（■え証することがてきる。
本発明の特徴（ユ、反応の全工程か極めて温和な反応条
件で進行するため、反応途中における置換基の転移や副
生物の生成か少なζ、出発原料として１重用する２−エ
テニルヘンスアミ１〜類の置換１．（の泣訴かそのまま
維持されて相当する１−イソキノリン類を高純度かつ好
収率て得ることかてきる。
以１ζ、本発明を実施例によりさらに詳細に説明゛りる
。
（実施例１）
マグネッチクスタラーと酸素カスを入れ／こコム風船を
装着しノ：：５０ｍ１フラスコに塩化パラジウム０２−
１８τ−、’ （１，４ｍｍｏｌ ）と塩化第一銅］、
、 ３８６ ｇ（１４ｍｍｏｌ ）を入れた。次いで、
２−エテニルヘンスアミＦ ２．０５８ ｇ （１４ｍ
ｍｏｌ）とｌ、３−プロパンジオール１ ｍｌ （１４
ｍｍｏｌ）を溶解した１２−ジェトキシ正タン２５ｍ１
を、：れに加え、酸素雰囲気下５０〜６０″Ｃで２４時
間攪拌した。反応流を冷却した後、エーテルを］、００
ｍ１を加えて不溶物を濾過により除去Ｌ ７’、。濾液
をシリカゲルカラムクロマトクラフィーにかけ、１−イ
ソキノリンの無色結晶１．−４９０ｇ（収率７３″３≦
〉を得た。
このものの融点を測定すると、２０ つ−２１０℃（文
献値・２０８ ’Ｃ）であった。
実施ρ１２〜６
実施例１と同様にして、各種の１−イソキノリン類を身
代した。その結果を第↓表に示す。
（以Ｆ余白）[Problems to be Solved by the Invention] The object of the present invention is to produce [isoquinoli] having a direct substituent at the 5-8 position of the 1-, isoquinoline ring under mild conditions with high purity and good acidity. 4. - To provide a method for manufacturing. [Means for Solving the Problems] In other words, the present invention is based on the general formula <I) elementary atom, fluorine atom, chlorine atom, 1 alkino group having 1 to 3 carbon atoms, 1 to 3 carbon atoms, The alkoxy group of 3, 2) ~oral- and 2-nibnylbenzamide 1~ represented by ``Sial A-lylaminosulfonyl group'' is mixed with palladium chloride and a salt 1. General formula (H) [wherein 'R1,F? , 2, R3, R, 4 are the same as defined above.] The present invention relates to a method for producing isoquinolines. The 1-ine quinolines obtained by the present invention are unsubstituted 1-isoquinolines and coisoquinolines having substituents on the Hensen ring. Substituent (represents a fluorine atom, a chlorine atom, an alkyl group having 1 to 3 carbon atoms, a 1 to 3 carbon atom,
~3 alkoxy group, 21 hero group and dialkylaminosulfonyl group, at least one substitution at any position from 5 to 8! Specifically, the coisoquinolines that can be printed according to the present invention include 1-isoquinoli〉', 6-fluoro-1 isoquinoline, 5-chloro-1-isoquinoline, 7-chloro-1
-isoquinolin>, 5-methyl]-inquinoline, 6-methyl-1-isoquinonone, 7-methyl-1-isoquinoline, 8-methyl-1-isoquinoline, 6-methyhex-1-isoquinoline, 7-methyl Examples include 1-xy-1-isoquinoline, 62-1-rho-j-isoquinoline, and 6-dimethylaminosulfonyl-1-isoquinoline. The 2-ethenylhenzamides represented by the general formula (I), which serve as the starting material for the present invention, are obtained by reacting 2-furo-18benzamide with ethylene residue in the presence of a palladium acetate catalyst. (R, F, Heck, Org, React,
2734.5. (], 982) ). The present invention produces 1-inquinolines of the general formula (II) by subjecting 2-ethenylbenzamide to a cyclization reaction in the presence of palladium chloride, cuprous chloride, and alcohol in an oxygen atmosphere. This is a method of manufacturing. The reaction of oxidizing an olefin compound using a palladium complex catalyst to form a carbonyl compound involves the formation of a wax between the shells.
The reaction is known as the Warakah reaction of styrene derivatives, which is usually ace1-phenone derivatives or lt'A. As a result of intensive research into the oxidation reaction of styrene derivatives using palladium complex catalysts, the inventors discovered that 2-ethynyl was converted to 2-ethynyl in the presence of alcohol using cuprous chloride as a cocatalyst. It was discovered that 1-isoquinolines can be efficiently converted using a palladium catalyst, and this led to the completion of the present invention. The alcohols used in the method of the present invention include lower alcohols such as methanol, ethanol, propane, phthanol, glycol,
], 3-p) Any of the tuffcols with an edge > 5 all may be used.
・(, l raw material name 1 and 2 1-100 mol 0°, salt f 1st phase is 1-2 times mol f heavy 3-ro σ) or -L arunia -IL, is 22 It is preferable to use ~1-15 moles of -ethenylhenzamites, and the solvent and 1-diolene, Tel-Rahi I. Loeffler>, 1.
, 2-simethoxyethoxy are suitable. The reaction of the present invention is carried out in the presence of K wood-containing ζr at normal pressure.
The process progresses easily by heating and stirring at 10 to 80°C. The first step of the reaction is recrystallization, column chromatography, and general purification methods such as column chromatography.
1 can be demonstrated (■).Characteristics of the present invention (Y) Since all steps of the reaction proceed under extremely mild reaction conditions, transfer of substituents during the reaction and generation of by-products are minimal. Substitution 1 of 2-ethenylhensaminia 1 to 1, which is used as a raw material, can be maintained as it is to obtain the corresponding 1-isoquinolines with high purity and good yield. Hereinafter, 1ζ, this book The invention will be explained in more detail with reference to examples. (Example 1) A 50 ml flask was filled with palladium chloride 0.2-.
18τ-,' (1.4 mmol) and cuprous chloride],
, 386 g (14 mmol) was added. Then,
2-ethenylhensami F 2.058 g (14m
mol) and 1 ml of l,3-propanediol (14
25 ml of 12-jetoxyprotane dissolved in mmol)
was added to : and stirred for 24 hours at 50-60"C under oxygen atmosphere. After cooling the reaction stream, the ether was added to ], 00
Add m1 and remove insoluble matter by filtration L7'. The filtrate was subjected to silica gel column chromatography to obtain colorless crystals of 1-isoquinoline. -490g (yield 73″3≦
> obtained. When the melting point of this product was measured, it was 20-210°C (literature value: 208'C). Examples ρ12 to 6 In the same manner as in Example 1, various 1-isoquinolines were substituted. The results are shown in Table ↓. (below F margin)
本発明により、 ６ＴＥ来合成が困難であった５〜８ 位に置換基を持つ１ イソキノリン類を高純度か つ好収率で得ることかできる。 According to the present invention, 5-8 that were difficult to synthesize since 6TE 1 with a substituent in position Are isoquinolines highly purified? It can be obtained in good yield.
Claims (1)
水素原子、フッ素原子、塩素原子、炭素数１〜３のアル
キル基、炭素数１〜３のアルコキシ基、ニトロ基および
ジアルキルアミノスルホニル基から選ばれる１種の基を
表す〕 で示される２−エテニルベンズアミド類を塩化パラジウ
ムと塩化第一銅およびアルコールの存在下、酸素雰囲気
中で反応させることを特徴とする一般式（II） ▲数式、化学式、表等があります▼（II） 〔式中、Ｒ＿１、Ｒ＿２、Ｒ＿３、Ｒ＿４は前記定義に
同じ〕 で示される１−イソキノリン類の製造方法。[Claims] 1) General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) [In the formula, R_1, R_2, R_3, and R_4 are hydrogen atoms, fluorine atoms, chlorine atoms, and carbon atoms, respectively. represents one type of group selected from an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a nitro group, and a dialkylaminosulfonyl group. General formula (II) characterized by reaction in the presence of copper and alcohol in an oxygen atmosphere ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) [In the formula, R_1, R_2, R_3, and R_4 are as defined above. Same as above] A method for producing a 1-isoquinoline represented by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1318488A JP2860676B2 (en) | 1989-12-07 | 1989-12-07 | Method for producing 1-isoquinolines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1318488A JP2860676B2 (en) | 1989-12-07 | 1989-12-07 | Method for producing 1-isoquinolines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03178966A true JPH03178966A (en) | 1991-08-02 |
| JP2860676B2 JP2860676B2 (en) | 1999-02-24 |
Family
ID=18099679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1318488A Expired - Fee Related JP2860676B2 (en) | 1989-12-07 | 1989-12-07 | Method for producing 1-isoquinolines |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2860676B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0569795A1 (en) * | 1992-05-12 | 1993-11-18 | Bayer Ag | Sulphonylbenzyl substituted benzo- and pyridopyridones |
-
1989
- 1989-12-07 JP JP1318488A patent/JP2860676B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0569795A1 (en) * | 1992-05-12 | 1993-11-18 | Bayer Ag | Sulphonylbenzyl substituted benzo- and pyridopyridones |
| US5354749A (en) * | 1992-05-12 | 1994-10-11 | Bayer Aktiengesellschaft | Sulfonylbenzyl-substituted benzo- and pyridopyridones |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2860676B2 (en) | 1999-02-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |