JPS62294656A - Novel dihydropyridine compound - Google Patents
Novel dihydropyridine compoundInfo
- Publication number
- JPS62294656A JPS62294656A JP31122586A JP31122586A JPS62294656A JP S62294656 A JPS62294656 A JP S62294656A JP 31122586 A JP31122586 A JP 31122586A JP 31122586 A JP31122586 A JP 31122586A JP S62294656 A JPS62294656 A JP S62294656A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- dimethyl
- group
- dihydropyridine
- 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
- -1 dihydropyridine compound Chemical class 0.000 title description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 abstract description 24
- 230000000694 effects Effects 0.000 abstract description 3
- 206010002383 Angina Pectoris Diseases 0.000 abstract description 2
- 206010020772 Hypertension Diseases 0.000 abstract description 2
- UKVYVZLTGQVOPX-IHWYPQMZSA-N (z)-3-aminobut-2-enoic acid Chemical class C\C(N)=C\C(O)=O UKVYVZLTGQVOPX-IHWYPQMZSA-N 0.000 abstract 1
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical class [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 abstract 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical class CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000002107 myocardial effect Effects 0.000 abstract 1
- 230000003449 preventive effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 7
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KXMSBUIIHMINLM-UHFFFAOYSA-N 2-(2-bromoethoxy)-5-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(OCCBr)C(C=O)=C1 KXMSBUIIHMINLM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XKORCTIIRYKLLG-ARJAWSKDSA-N methyl (z)-3-aminobut-2-enoate Chemical compound COC(=O)\C=C(\C)N XKORCTIIRYKLLG-ARJAWSKDSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、すぐれたカルシウム（Ｃａ”）拮抗作用と交
感神経β受容体遮断作用、場合により心臓選択性β受容
体（β１）遮断作用等を併有するジヒドロピリジン化合
物を製造するための中間体として有用な新規ジヒドロピ
リジン化合物に関する。Detailed Description of the Invention (Industrial Application Field) The present invention provides excellent calcium (Ca") antagonism, sympathetic β-receptor blocking action, and optionally cardioselective β-receptor (β1) blocking action, etc. The present invention relates to a novel dihydropyridine compound useful as an intermediate for producing a dihydropyridine compound having the following.
（発明の解決手段）
さらに詳しくは１本発明は、一般式
（式中、Ｒ′およびＲ２は同一または異って低級アルキ
ル基
Ｒ３およびＲ′は同一または異って低級アルキル基
Ａは低級アルキレン法
Ｘはハロゲン原子またはトンルオキシ基を意味する。）
で示されるジヒドロピリジン化合物またはその塩である
。(Means for Solving the Invention) More specifically, 1 the present invention relates to the general formula (wherein R' and R2 are the same or different, lower alkyl groups R3 and R' are the same or different, and the lower alkyl group A is lower alkylene Method X means a halogen atom or a tonloxy group.) A dihydropyridine compound or a salt thereof.
上記一般式のＲ１−Ｒ４の意味する低級アルキル基ハ、
メチル基、エチル基、イソプロピル基。A lower alkyl group represented by R1 to R4 in the above general formula,
Methyl group, ethyl group, isopropyl group.
ブチル基などの炭素数１乃至５個の直鎖状または分枝状
の炭化水素鎖である。また、Ａの意味する低級アルキレ
ン基は、メチレン基、エチレン基、フロピレン基、ブチ
レン゛基、ペンチレン基等炭素数１乃至５個の直鎖状の
炭化水素鎖である。さらに、Ｘの意味するハロゲン原子
は。It is a straight or branched hydrocarbon chain having 1 to 5 carbon atoms, such as a butyl group. Further, the lower alkylene group meant by A is a linear hydrocarbon chain having 1 to 5 carbon atoms, such as a methylene group, an ethylene group, a propylene group, a butylene group, and a pentylene group. Furthermore, the halogen atom represented by X is.
たとえば塩素原子、ブロム原子、ヨウ素原子などである
。Examples include chlorine atom, bromine atom, and iodine atom.
（従来の技術）
本発明の化合物（Ｉ）は、ジヒドロピリジン骨格の４位
に置換したニドフェニル基にハロゲノ低級アルコキシ基
またはトルエンスルホニルオキシ低級アルコキシ基を有
する点に化学構造上の特徴のある化合物であり、かかる
化合物を記載した文献は見当らない。(Prior Art) Compound (I) of the present invention is a compound characterized in its chemical structure in that the nidophenyl group substituted at the 4-position of the dihydropyridine skeleton has a halogeno lower alkoxy group or a toluenesulfonyloxy lower alkoxy group. , no literature describing such compounds has been found.
（製造法）
本発明の化合物は、つぎの反応式で示されろ方法によっ
て製造することができる。(Production method) The compound of the present invention can be produced by the method shown in the following reaction formula.
第一製法
（ｒ）
第二製法
（Ｉ）
第一製法の実施は、化合物（ＴＩ）と好ましくは等モル
の化合物（ＩＩＩ）および好ましくは等モルの化合物（
ＩＶ）とを無溶媒または不活性溶媒中で混合する。溶媒
としては、アルコール、ジオキサン、イノプロピルアル
コール、ジメチルポルムアミド、ジメチルスルホキシド
、アセトニトリルなどが使用できる。反応を促進するた
めに加熱するのが好ましい。First production method (r) Second production method (I) The first production method is carried out by combining compound (TI) with preferably equimolar amounts of compound (III) and preferably equimolar amounts of compound (III) with compound (TI).
IV) without a solvent or in an inert solvent. As the solvent, alcohol, dioxane, inopropyl alcohol, dimethylpolamide, dimethyl sulfoxide, acetonitrile, etc. can be used. Heating is preferred to accelerate the reaction.
なお、化合物（ＴＶ）は、あらかじめＲ’ Ｃ０ＣＨ，
ＣＯＯＲ２とアンモニア（ＮＨ３）とを反応させて得る
ことができ、生成した化合成（ｒＶ）は、一旦単離する
かあるいは単離せずしてそのまま化合物（ｎ）およびＧ
ｒｌ）とを反応させて目的化合物（Ｉ）に導くことがで
きる。In addition, the compound (TV) is prepared in advance by R′ C0CH,
It can be obtained by reacting COOR2 with ammonia (NH3), and the generated chemical synthesis (rV) can be isolated once or without isolation and used as it is with compound (n) and G
rl) to lead to the target compound (I).
また、第二製法に示されるように、あらかじめ化合物（
ｒＩ）と化合物（ｍ）とを反応させて得られる化合物（
Ｖ）を原料とし、これに化合物ＱＶ）を反応させる方法
によっても目的化合物（Ｉ）を製造することができろ。In addition, as shown in the second production method, the compound (
The compound obtained by reacting rI) with compound (m) (
The target compound (I) can also be produced by using V) as a raw material and reacting it with compound QV).
こうして得られた目的化合物は、たとえば抽出、結晶化
、カラムクロマトグラフィー等の通常の化学操作によっ
て単離精製できる。The target compound thus obtained can be isolated and purified by conventional chemical operations such as extraction, crystallization, and column chromatography.
（発明の効果）
本発明の化合物は、一般式
（式中、Ｒ’−Ｒ’、Ａは前記と同じ意味を表わす。Ｂ
は単結合または式−ＣＨ２０−で示される基を意味する
。）
で示されるジヒドロピリジン誘導体を製造するための原
料として有用である。この化合物（ＶＩ）は、副作用の
少い高血圧および狭心症や心筋梗塞などの予防及び治療
剤として重要であり、たとえば本発明の化合物（１）と
一般式Ｈ・Ｎ−ＣＨ，ＣＨ−Ｂ＜Ｉ＞♂Ｈ
（式中、Ｂは前記と同じ意味を表わす）で示されるアミ
ン誘導体とを反応させることによって製造することがで
きる（特開昭１３１−１２６６２号参照）。(Effects of the Invention) The compound of the present invention has the general formula (wherein R'-R' and A represent the same meanings as above.B
means a single bond or a group represented by the formula -CH20-. ) It is useful as a raw material for producing the dihydropyridine derivative shown below. This compound (VI) is important as a prophylactic and therapeutic agent for hypertension, angina pectoris, myocardial infarction, etc. with few side effects. It can be produced by reacting with an amine derivative represented by <I>♂H (in the formula, B represents the same meaning as above) (see JP-A-131-12662).
（実施例） 以下９本発明をさらに具体的に説明するため。(Example) The following 9 examples will further specifically explain the present invention.
実施例を掲記する。Examples are listed below.
実施例 １
２−（２−ブロモエトキシ）−５−ニトロベンズアルデ
ヒド２３．ｇ、 ３−アミノクロトン酸メチル１１．
５ｇおよびアセト酢酸メチル１１．６ｇをインプロパツ
ールに溶解し７時間加熱還流する。冷却後。Example 1 2-(2-bromoethoxy)-5-nitrobenzaldehyde 23. g, methyl 3-aminocrotonate 11.
5 g and 11.6 g of methyl acetoacetate were dissolved in Impropatol and heated under reflux for 7 hours. After cooling.
析出した結晶を炉取してメタノールで洗い、風乾し、ジ
メチル４−［（２−ブロモエトキシ）−５−二トロフェ
ニル］−２，６−シメチルー１，４−ジヒドロピリジン
−３，５−ジカルボキシレートの粗結晶を３３ｇ得た。The precipitated crystals were collected in a furnace, washed with methanol, air-dried, and dimethyl 4-[(2-bromoethoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxy 33 g of crude crystals of Rate were obtained.
本化合物の生成は、この化合物を以下の方法により、対
応するアミン誘導体
に導くことにより確認した。The production of this compound was confirmed by converting this compound into the corresponding amine derivative by the following method.
（イ） ジメチル４−［（２−ブロモエトキシ）−５−
ニトロフェニル］−２＋６−シメチルー１１４−ジヒド
ロピリジン−３，５−ジカルボキシレート１７ｇおよび
フタルイミドカリウム７４ｇをＮ、Ｎ−ジメチルホルム
アミド２５ ｍｌに懸濁し、１２０〜１３０°Ｃで３時
間加熱する。反応液を氷水７５０ ｍｌに注加して析出
した結晶を戸数する。水洗、風乾し、ジメチル ＝４−
［（２−フタルイミドエトキシ）−５−ニトロフェニル
］ −２，６−シメチルー１．・１−ジヒドロピリジン
−３，５−ジカルボキレートの粗結晶１９．６ｇを得た
。(a) Dimethyl 4-[(2-bromoethoxy)-5-
17 g of nitrophenyl]-2+6-dimethyl-114-dihydropyridine-3,5-dicarboxylate and 74 g of potassium phthalimide are suspended in 25 ml of N,N-dimethylformamide and heated at 120-130° C. for 3 hours. Pour the reaction solution into 750 ml of ice water and count the precipitated crystals. Wash with water, air dry, dimethyl = 4-
[(2-phthalimidoethoxy)-5-nitrophenyl] -2,6-cymethyl-1. - 19.6 g of crude crystals of 1-dihydropyridine-3,5-dicarboxylate were obtained.
（ロ） ジメチル ４−［（２−フタルイミドエトキシ
）−５−ニトロフェニル］−２，６−’；メチルー１，
４−ジヒドロピリジン−３＋５−ジカルボキシレー）１
２ｇ、ヒドラジン１水和物６ ｍｌおよびエタノール２
４０ ｍｌの溶液を還流下３０分間加熱する。析出した
結晶を熱時戸去し、Ｐ液を減圧下溶媒を留去する。残渣
に水を加え、酢酸エチルで抽出し、抽出液を水洗。(b) Dimethyl 4-[(2-phthalimidoethoxy)-5-nitrophenyl]-2,6-'; Methyl-1,
4-dihydropyridine-3+5-dicarboxylene)1
2 g, 6 ml hydrazine monohydrate and 2 ml of ethanol
Heat 40 ml of the solution under reflux for 30 minutes. The precipitated crystals are removed while hot, and the solvent of the P solution is distilled off under reduced pressure. Water was added to the residue, extracted with ethyl acetate, and the extract was washed with water.
無水硫酸ナトリウムで乾燥後、溶媒を留去する。得られ
た粗結晶をメタノールから再結晶し、ジメチル４−［２
−（２−アミノエトキシ）−５−二トロフェニル］
２＋６−シメチルーＬ、！−ジヒロピリジ／−３１５−
ジカルボキシレートを６ｇ得た。この化合物は次の理化
学的性状を有する。After drying over anhydrous sodium sulfate, the solvent is distilled off. The obtained crude crystals were recrystallized from methanol and dimethyl 4-[2
-(2-aminoethoxy)-5-nitrophenyl]
2+6-cymethyl-L,! -dihydropyridi/-315-
6 g of dicarboxylate was obtained. This compound has the following physical and chemical properties.
（１）融点 ２２８〜２３０°Ｃ
（１１） 元素分析値（ＣＩＱ Ｎ２３ Ｎ３ ｏ７
として）Ｃ（％） Ｈ（％）Ｎ（％）
計算値 ５６，２９ ５．７２ １０．３６実測
値 ５６，０６ ５．８２ １０．１０（ｉｉＤ
核磁気共鳴スペクト＃ （ｄ６− ＤＭＳＯ）δ（
ｐｐｍ） ； ２．２４ （６Ｈ，！り２．９４ （２
Ｈ，ｔ）
３．４８ （６Ｈ，！ｌ）
４．０６ （２Ｈ，ｔ）
５．２４ （ＩＨ，！り
実施例 ２
２−（２−ブロモエトキシ）−５−ニトロベンズアルデ
ヒド２３ｇ、３−アミノクロトン酸メチル１１．５ ｇ
およびアセト酢酸メチル１１６ｇを原料とし。(1) Melting point 228-230°C (11) Elemental analysis value (CIQ N23 N3 o7
) C (%) H (%) N (%) Calculated value 56,29 5.72 10.36 Actual value 56,06 5.82 10.10 (iiD
Nuclear magnetic resonance spectrum # (d6-DMSO) δ(
ppm) ; 2.24 (6H,!ri2.94 (2
H, t) 3.48 (6H, !l) 4.06 (2H, t) 5.24 (IH,! Example 2 2-(2-bromoethoxy)-5-nitrobenzaldehyde 23 g, 3-amino Methyl crotonate 11.5 g
and 116 g of methyl acetoacetate as raw materials.
実施例１と同様に処理してジメチル ４−［（２−ブロ
モエトキシ）−５−ニトロフェニル］ −２゜６−シメ
チルー１．４−ジヒドロピリジン−３＋５−ジカルボキ
シレートの粗結晶３５ ｇを得た。融点２４７〜２５０
’Ｃ（メタノールで洗浄）。The same procedure as in Example 1 was carried out to obtain 35 g of crude crystals of dimethyl 4-[(2-bromoethoxy)-5-nitrophenyl]-2゜6-dimethyl-1,4-dihydropyridine-3+5-dicarboxylate. . Melting point 247-250
'C (washed with methanol).
Claims (1)
ルキル基 Ｒ＾３およびＲ＾４は同一または異って低級アルキル基 Ａは低級アルキレン基 Ｘはハロゲン原子またはトシルオキシ基 を意味する。） で示されるジヒドロピリジン化合物またはその塩。[Claims] General formula▲ Numerical formula, chemical formula, table, etc.▼ (In the formula, R^1 and R^2 are the same or different, and lower alkyl groups R^3 and R^4 are the same or different. (lower alkyl group A means lower alkylene group X means halogen atom or tosyloxy group) or a salt thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31122586A JPS62294656A (en) | 1986-12-26 | 1986-12-26 | Novel dihydropyridine compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31122586A JPS62294656A (en) | 1986-12-26 | 1986-12-26 | Novel dihydropyridine compound |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59133650A Division JPS6112662A (en) | 1984-06-28 | 1984-06-28 | Dihydropyridine derivative and its production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62294656A true JPS62294656A (en) | 1987-12-22 |
| JPH02351B2 JPH02351B2 (en) | 1990-01-08 |
Family
ID=18014598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP31122586A Granted JPS62294656A (en) | 1986-12-26 | 1986-12-26 | Novel dihydropyridine compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62294656A (en) |
-
1986
- 1986-12-26 JP JP31122586A patent/JPS62294656A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02351B2 (en) | 1990-01-08 |
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