JPS6041075B2 - Pyridine derivative - Google Patents
Pyridine derivativeInfo
- Publication number
- JPS6041075B2 JPS6041075B2 JP55016952A JP1695280A JPS6041075B2 JP S6041075 B2 JPS6041075 B2 JP S6041075B2 JP 55016952 A JP55016952 A JP 55016952A JP 1695280 A JP1695280 A JP 1695280A JP S6041075 B2 JPS6041075 B2 JP S6041075B2
- Authority
- JP
- Japan
- Prior art keywords
- pyridine derivative
- compound
- general formula
- present
- pyridine
- 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.)
- Expired
Links
- 150000003222 pyridines Chemical class 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- -1 5-substituted hexahydro-3aH-pyrrolo[3.2-C]pyridine Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 2
- 239000003874 central nervous system depressant Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar 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
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
【発明の詳細な説明】
本発明は次の一般式〔１〕で表わされるピリジン誘導体
に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a pyridine derivative represented by the following general formula [1].
ただし、Ｒは低級アルキル又は （ｍは１又は２を麦わ す。However, R is lower alkyl or (m stands for 1 or 2) vinegar.
）を表わす。本発明化合物は文献末教の新規化合物であ
り「中枢抑制作用、特に鎮痛作用を有する１０−オキソ
ー２アザェリスリナン誘導体の合成中間体として極めて
有用である。). The compound of the present invention is a novel compound disclosed in the literature and is extremely useful as an intermediate for the synthesis of 10-oxo-2 azaerythrinane derivatives having central depressant action, particularly analgesic action.
本発明化合物は種々の方法によって製造することができ
るが、一般式〔ロ〕〔式中Ｒは前記と同じ。）で示され
る化合物の保護基であるエチレンジオキシ基を脱保護し
てカルボニル基にすれば同時に同一分子内のアミノ＊基
と縮合して収率よく得られることができる。The compound of the present invention can be produced by various methods, and is represented by the general formula [B] [wherein R is the same as above]. ) If the ethylenedioxy group, which is the protective group, of the compound represented by the formula is deprotected to form a carbonyl group, it can be simultaneously condensed with an amino* group in the same molecule and obtained in good yield.
脱保護の条件は一般的な加水分解条件、たとえば鍵酸中
で加熱することにより容易に行える。本発明化合物は、
たとえば一般式〔ｍ〕で表わされるフェニル酢酸誘導体
と反応させて〔Ｗ〕となし、ついで酸性条件下で加熱閉
環せしめれば１０ーオキソー２アザェＩＪスリナン誘導
体〔Ｖ〕となすことができる。Deprotection conditions can be easily carried out under general hydrolysis conditions, such as heating in key acid. The compound of the present invention is
For example, by reacting with a phenylacetic acid derivative represented by the general formula [m] to form [W], and then ring-closing by heating under acidic conditions, a 10-oxo-2azae IJ surinane derivative [V] can be obtained.
Ｒ，，Ｒ２は水素又は低級アルコキシを表わす。R,,R2 represent hydrogen or lower alkoxy.
Ｘはハロゲン又は−ＯＣ０２Ｒ３（Ｒ３はアルキル）を
表わす。〔Ｖ〕は文献未萩の新規化合物であって、中枢
抑制作用、特に強い鎮痛作用を有している。X represents halogen or -OC02R3 (R3 is alkyl). [V] is a novel compound that has not yet been published in the literature, and has a central depressant effect, particularly a strong analgesic effect.
以下に本発明化合物の製造に関する実施例を掲げる。実
施例 １
２，３，４，５，６，７−へキサハイドロ−５−メチル
−＄Ｈ−ビロロ〔３．２−Ｃ〕ビリジン３−（２ーアミ
ノエチル）一４，４ーエチレンジオキシー１−メチルピ
ベリジン３．０夕を１０％塩酸３０の‘に溶解し６時間
加熱還流する。Examples related to the production of the compounds of the present invention are listed below. Example 1 2,3,4,5,6,7-hexahydro-5-methyl-$H-virolo[3.2-C]pyridine 3-(2-aminoethyl)-4,4-ethylenedioxy-1- 3.0 ml of methylpiveridine was dissolved in 3.0 ml of 10% hydrochloric acid and heated under reflux for 6 hours.
冷後、反応援を氷冷し炭酸カリウムで中和して遊離物を
クロロホルムで抽出、飽和食塩水で洗浄、乾燥してクロ
ロホルムを蟹去する。残留物を減圧蒸留する。ｂｐ５１
〜３℃／３側Ｈｇ 得量＝１．０夕簿層クロマトグラフ
ィー（シリカゲルプレート、展開溶媒メタノール）：Ｒ
ｆ≠０．３８ＮＭＲ（ＣＤＣ１３）６：４．０〜１．１
７（ｍ，１１Ｈ），２．３５（Ｓ，畑）ＩＲレ点纂ｔ肌
‐１：２７８０，２７４０，１６５５実施例 ２２，３
，４，５，６，７−へキサハイドロー５−フエネチル−
粉Ｈ−ピロロ〔３‐２一Ｃ〕ピリジン３一（２−アミノ
エチル）−４，４ーエチレンジオキシ−１一フエネチル
ピベリジン２．９夕を２０％塩酸１５の‘に溶解し５時
間加熱還流する。After cooling, the solution is cooled on ice, neutralized with potassium carbonate, and the free substances are extracted with chloroform, washed with saturated saline, and dried to remove the chloroform. The residue is distilled under reduced pressure. bp51
~3°C/3 side Hg Yield = 1.0 Length layer chromatography (silica gel plate, developing solvent methanol): R
f≠0.38NMR (CDC13) 6:4.0-1.1
7 (m, 11H), 2.35 (S, field) IR spot-spotted skin-1: 2780, 2740, 1655 Example 22, 3
,4,5,6,7-hexahydro-5-phenethyl-
Powdered H-pyrrolo[3-21C]pyridine 3-(2-aminoethyl)-4,4-ethylenedioxy-1-phenethyl piveridine was dissolved in 15% of 20% hydrochloric acid. Heat to reflux for 5 hours.
Claims (1)
ドロ−３ａＨ−ピロロ〔３．２−Ｃ〕ピリジン誘導体。 ▲数式、化学式、表等があります▼ ただし、Ｒは低級アルキル又は ▲数式、化学式、表等があります▼ （ｍは１又は２を表わ す。 ）を表わす。[Scope of Claims] 1. A 5-substituted hexahydro-3aH-pyrrolo[3.2-C]pyridine derivative represented by the following general formula [I]. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ However, R represents lower alkyl or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (m represents 1 or 2).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55016952A JPS6041075B2 (en) | 1980-02-13 | 1980-02-13 | Pyridine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55016952A JPS6041075B2 (en) | 1980-02-13 | 1980-02-13 | Pyridine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56113781A JPS56113781A (en) | 1981-09-07 |
| JPS6041075B2 true JPS6041075B2 (en) | 1985-09-13 |
Family
ID=11930451
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55016952A Expired JPS6041075B2 (en) | 1980-02-13 | 1980-02-13 | Pyridine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6041075B2 (en) |
-
1980
- 1980-02-13 JP JP55016952A patent/JPS6041075B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56113781A (en) | 1981-09-07 |
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