JPS596856B2 - Glycerol - Google Patents
GlycerolInfo
- Publication number
- JPS596856B2 JPS596856B2 JP50040881A JP4088175A JPS596856B2 JP S596856 B2 JPS596856 B2 JP S596856B2 JP 50040881 A JP50040881 A JP 50040881A JP 4088175 A JP4088175 A JP 4088175A JP S596856 B2 JPS596856 B2 JP S596856B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- substituent
- general formula
- glycerol
- derivative represented
- 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title 3
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 150000002314 glycerols Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical class COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- -1 methoxyphenyl Chemical group 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- IWPZKOJSYQZABD-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical class COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 description 1
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical class COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- JJQPNZTWSXLKER-UHFFFAOYSA-M sodium;3,4,5-trimethoxybenzoate Chemical compound [Na+].COC1=CC(C([O-])=O)=CC(OC)=C1OC JJQPNZTWSXLKER-UHFFFAOYSA-M 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000002471 thromboprophylactic effect Effects 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000001680 trimethoxyphenyl group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Landscapes
- Quinoline Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【発明の詳細な説明】 本発明はグリセロール誘導体の製造法に関する。[Detailed description of the invention] The present invention relates to a method for producing glycerol derivatives.
本発明により得られるグリセロール誘導体は一般式（式
中Ｒ２は置換基として低級アルコキシ基を有するフェニ
ル基を示す。The glycerol derivative obtained by the present invention has the general formula (wherein R2 represents a phenyl group having a lower alkoxy group as a substituent.
）で表わされる化合物である。本発明の上記化合物は文
献未載の新規化合物であり、抗炎症作用、血小板凝集抑
制作用を有し消炎薬、血栓予防薬として有用である。) is a compound represented by The above-mentioned compound of the present invention is a novel compound that has not been described in any literature, and has anti-inflammatory effects and platelet aggregation-inhibiting effects, and is useful as an anti-inflammatory drug and a thromboprophylactic drug.
本発明に係るグリセロール誘導体は一般式（式中Ｒ１は
置換基として低級アルキル基を有するフエニル基を示す
。The glycerol derivative according to the present invention has the general formula (wherein R1 represents a phenyl group having a lower alkyl group as a substituent.
）で表わされる３・４−ジヒドロカルボスチリル誘導体
と、一般式（式中Ｒ２は置換基として低級アルコキシ基
を有するフエニル基、Ｍはアルカリ金属を示す。) and a 3,4-dihydrocarbostyryl derivative represented by the general formula (wherein R2 is a phenyl group having a lower alkoxy group as a substituent, and M represents an alkali metal).
）で表わされるカルボン酸誘導体を反応させることによ
り製造される。本発明の出発物質である式（１）の３・
４−ジヒドロカルボスチリル誘導体は公知の化合物であ
り、置換基Ｒ１としてはトリル、キシリル等の置換基と
して低級アルキル基を有するフエニル基を例示出来る。) is produced by reacting a carboxylic acid derivative represented by 3 of formula (1), which is the starting material of the present invention.
The 4-dihydrocarbostyryl derivative is a known compound, and examples of the substituent R1 include a phenyl group having a lower alkyl group as a substituent such as tolyl and xylyl.
式（１）で表わされる３・４−ジヒドロカルボスチリル
誘導体の具体例としては、例えば１−（３・４−ジヒト
ロー５−カルボスチリノ（ハ）オキシ−３−（Ｐ−トル
エンスルホンオキシ）プロパン−２−オール等を代表例
として挙げることができる。本発明のもう一方の出発物
質である式（）のカルボン酸誘導体も公知の化合物であ
り、置換基Ｒ２としては例えばメトキシフエニル、トリ
メトキシフエニル等の置換基として低級アルコキシ基を
有すケフエニル基があり、Ｍはアルカリ金属である。Specific examples of the 3,4-dihydrocarbostyryl derivative represented by formula (1) include 1-(3,4-dihydro-5-carbostyrino(ha)oxy-3-(P-toluenesulfonoxy)propane-2). The other starting material of the present invention, the carboxylic acid derivative of formula (), is also a known compound, and the substituent R2 is, for example, methoxyphenyl, trimethoxyphenyl. There is a kephenyl group having a lower alkoxy group as a substituent, and M is an alkali metal.
式（）で表わされるカルボン酸誘導体の具体例としては
、例えばＰ−メトキシ安息香酸、３・４・５−トリメト
キシ安息香酸等のナトリウム塩、カリウム塩等を挙げる
ことができる。本発明の反応において上記式（１）で表
わされる３・４−ジヒドロカルボスチリル誘導体と式（
）で表わされるカルボン酸誘導体の使用割合は広く適宜
に選択できるが通常は後者に対して前者を等モル〜５倍
モル、好ましくは等モル〜２倍モル用いるのが望ましい
。本反応は無溶媒下、溶媒の存在下いずれでも行なうこ
とができるが、一般には溶媒の存在下に行なうのが好ま
しい。Specific examples of the carboxylic acid derivative represented by formula () include sodium salts and potassium salts of P-methoxybenzoic acid, 3,4,5-trimethoxybenzoic acid, and the like. In the reaction of the present invention, the 3,4-dihydrocarbostyryl derivative represented by the above formula (1) and the formula (
Although the proportion of the carboxylic acid derivative represented by ) can be appropriately selected from a wide range, it is usually desirable to use the former in moles equivalent to 5 times the mole of the latter, preferably equimolar to 2 times the mole of the latter. Although this reaction can be carried out either in the absence of a solvent or in the presence of a solvent, it is generally preferable to carry out it in the presence of a solvent.
溶媒としては反応に関与しない溶媒であればいずれも使
用できるが、例えばメタノール、エタノール、プロパノ
ール等のアルコール類、ジエチルエーテル、テトラヒド
ロフラン、ジオキサン、エチレングリコールモノメチル
エーテル等のエーテル類、ベンゼン、トルエン、キシレ
ン、クロルベンゼン等の芳香族炭化水素類、Ｎ・Ｎ−ジ
メチルホルムアミド、ジメチルスルホキシド、ヘキサメ
チルリん酸トリアミド等の非プロトン性極性溶媒等の溶
媒が有利に用いられる。本反応において反応温度は特に
限定されないが、一般に加温ないしは加熱下に行なわれ
、好ましくは室温〜１５０℃の温度で行なうのが望まし
い。以上のようにして得られる本発明化合物は沢過、洗
浄、再結晶等の公知の手段によつて分離、精製すること
ができる。以下に本発明の実施例を挙げる。As the solvent, any solvent that does not participate in the reaction can be used, such as alcohols such as methanol, ethanol, and propanol, ethers such as diethyl ether, tetrahydrofuran, dioxane, and ethylene glycol monomethyl ether, benzene, toluene, xylene, Solvents such as aromatic hydrocarbons such as chlorobenzene, aprotic polar solvents such as N.N-dimethylformamide, dimethylsulfoxide, and hexamethylphosphoric triamide are advantageously used. Although the reaction temperature in this reaction is not particularly limited, it is generally carried out with heating or under heating, preferably at a temperature of room temperature to 150°C. The compound of the present invention obtained as described above can be separated and purified by known means such as filtration, washing, and recrystallization. Examples of the present invention are listed below.
実施例 １
１−（３・４−ジヒトロー５−カルボスチリル）オキシ
−３−（Ｐ−トルエンスルホンオキシ）プロパン−２−
オール（融点９３〜９６℃）１４７及びナトリウム・−
３・４・５−トリメトキシベンゾエート１５．４７をＮ
−Ｎ−ジメチルホルムアミド３００ｍ１に加えて１００
〜１１０℃にて４時間加熱撹拌する。Example 1 1-(3,4-dihythro-5-carbostyryl)oxy-3-(P-toluenesulfonoxy)propane-2-
All (melting point 93-96℃) 147 and sodium -
3,4,5-trimethoxybenzoate 15.47N
-N-dimethylformamide 300ml plus 100ml
Heat and stir at ~110°C for 4 hours.
反応後反応液を水２０００ｍ１中に注ぎ析出した結晶を
沢取する。得られた結晶をエタノールから再結晶し無色
針状晶の１−（３・４ジヒトロー５−カルボスチリル）
オキシ−３−（３・４・５−トリメトキシベンゾイルオ
キシ）プロパン−２−オール１２７を得る。融点１７５
〜１７８℃After the reaction, the reaction solution was poured into 2000 ml of water and the precipitated crystals were collected. The obtained crystals were recrystallized from ethanol to obtain colorless needle-like crystals of 1-(3,4-dihydro-5-carbostyryl).
Oxy-3-(3.4.5-trimethoxybenzoyloxy)propan-2-ol 127 is obtained. Melting point 175
~178℃
Claims (1)
ェニル基を示す。 ）で表わされる３・４−ジヒドロカルボスチリル誘導体
と、一般式Ｒ＾２ＣＯＯＭ （式中Ｒ＾２は置換基として低級アルコキシ基を有する
フェニル基、Ｍはアルカリ金属を示す。 ）で表わされるカルボン酸誘導体とを反応させ一般式▲
数式、化学式、表等があります▼（式中Ｒ＾２は上記に
同じ。 ）で表わされるグリセロール誘導体を得ることを特徴と
するグリセロール誘導体の製造法。[Claims] 1 3,4-dihydrocarbostyryl represented by the general formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (In the formula, R^1 represents a phenyl group having a lower alkyl group as a substituent.) The derivative is reacted with a carboxylic acid derivative represented by the general formula R^2COOM (in the formula, R^2 is a phenyl group having a lower alkoxy group as a substituent, and M represents an alkali metal) to form the general formula ▲.
A method for producing a glycerol derivative, which is characterized by obtaining a glycerol derivative represented by a mathematical formula, a chemical formula, a table, etc. (in the formula, R^2 is the same as above).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50040881A JPS596856B2 (en) | 1975-04-03 | 1975-04-03 | Glycerol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50040881A JPS596856B2 (en) | 1975-04-03 | 1975-04-03 | Glycerol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51115483A JPS51115483A (en) | 1976-10-12 |
| JPS596856B2 true JPS596856B2 (en) | 1984-02-15 |
Family
ID=12592838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50040881A Expired JPS596856B2 (en) | 1975-04-03 | 1975-04-03 | Glycerol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS596856B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5384978A (en) * | 1976-12-29 | 1978-07-26 | Otsuka Pharmaceut Co Ltd | Carbostyril derivative |
-
1975
- 1975-04-03 JP JP50040881A patent/JPS596856B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51115483A (en) | 1976-10-12 |
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