JPS6312466B2 - - Google Patents
Info
- Publication number
- JPS6312466B2 JPS6312466B2 JP12752780A JP12752780A JPS6312466B2 JP S6312466 B2 JPS6312466 B2 JP S6312466B2 JP 12752780 A JP12752780 A JP 12752780A JP 12752780 A JP12752780 A JP 12752780A JP S6312466 B2 JPS6312466 B2 JP S6312466B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- benzoic acid
- melting point
- carboxyphenyl
- imino
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- -1 o-carboxyphenyl Chemical group 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- JKNKNWJNCOJPLI-UHFFFAOYSA-N o-phthalaldehydic acid Chemical compound C1=CC=C2C(O)OC(=O)C2=C1 JKNKNWJNCOJPLI-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JYYLQSCZISREGY-UHFFFAOYSA-N 2-amino-4-chlorobenzoic acid Chemical compound NC1=CC(Cl)=CC=C1C(O)=O JYYLQSCZISREGY-UHFFFAOYSA-N 0.000 description 1
- NBUUUJWWOARGNW-UHFFFAOYSA-N 2-amino-5-methylbenzoic acid Chemical compound CC1=CC=C(N)C(C(O)=O)=C1 NBUUUJWWOARGNW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010018910 Haemolysis Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940054441 o-phthalaldehyde Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Description
【発明の詳細な説明】
本発明は一般式（）
（式中、R1は水素原子及び任意の位置に１〜
２個置換したハロゲン原子、低級アルキル基、低
級アルコキシ基、ニトロ基を、ＸはCH又はＮ原
子を、R2は水素原子又は低級アルキル基を意味
する）で表わされる新規な安息香酸誘導体に関す
るものである。[Detailed Description of the Invention] The present invention relates to the general formula () (In the formula, R 1 is a hydrogen atom and 1 to
A new benzoic acid derivative represented by a disubstituted halogen atom, lower alkyl group, lower alkoxy group, or nitro group, where X is a CH or N atom, and R2 is a hydrogen atom or a lower alkyl group) It is.
前記一般式（）で表わされる本発明の安息香
酸誘導体は文献未載の新規化合物であり、抗炎症
作用、抗リウマチ作用、抗アレルギー作用、溶血
反応阻害作用等の薬理作用を有し、医薬品として
産業上有用な化合物である。 The benzoic acid derivative of the present invention represented by the above general formula () is a new compound that has not been described in any literature, and has pharmacological effects such as anti-inflammatory effect, anti-rheumatic effect, anti-allergic effect, and hemolytic reaction inhibition effect, and can be used as a pharmaceutical. It is an industrially useful compound.
前記一般式（）におけるR1及びR2に就いて
更に具体的に説明すると、R1のハロゲン原子と
しては弗素、塩素、臭素、沃素等が、又、R1の
低級アルキル基としてはメチル、エチル、プロピ
ル等が、更にR1の低級アルコキシ基としてはメ
トキシ、エトキシ等が挙げられる。次にR2の低
級アルキル基としてはメチル、エチル、ｎ―プロ
ピル、イソプロピル、ｎ―ブチル、イソブチル等
が挙げられる。 To explain R 1 and R 2 in the general formula () more specifically, the halogen atom of R 1 is fluorine, chlorine, bromine, iodine, etc., and the lower alkyl group of R 1 is methyl, Examples of the lower alkoxy group of R 1 include ethyl and propyl, and examples of the lower alkoxy group for R 1 include methoxy and ethoxy. Examples of the lower alkyl group for R 2 include methyl, ethyl, n-propyl, isopropyl, n-butyl, and isobutyl.
本発明の化合物は下記の反応式で示す如く、一
般式（）のアントラニル酸誘導体と式（）の
ｏ―フタルアルデヒド酸の等モルをメタノール、
エタノール、テトラヒドロフラン、ジオキサン、
ベンゼン、トルエン、キシレン等の溶媒中、室温
又は加熱下に反応させることにより短時間で反応
が進行し、好収率で前記一般式（）で示される
安息香酸誘導体を得ることが出来る。 As shown in the reaction formula below, the compound of the present invention is prepared by mixing equimolar amounts of an anthranilic acid derivative of general formula () and o-phthalaldehyde acid of formula () with methanol,
Ethanol, tetrahydrofuran, dioxane,
By carrying out the reaction in a solvent such as benzene, toluene, xylene, etc. at room temperature or under heating, the reaction proceeds in a short time, and the benzoic acid derivative represented by the general formula () can be obtained in a good yield.
（式中、R1，Ｘ及びR2は前記と同じ意味を有
する）
以下に実施例を示して本発明を具体的に説明す
る。 (In the formula, R 1 , X and R 2 have the same meanings as described above.) The present invention will be specifically explained below with reference to Examples.
実施例 １
４―クロルアントラニル酸1.7ｇとｏ―フタル
アルデヒド酸1.5ｇをメタノール50mlに加え室温
で１時間撹拌した。次いで溶媒を濃縮し、析出す
る結晶を取、乾燥すると無色プリズム晶の２―
｛〔（ｏ―カルボキシフエニル）イミノ〕メチル｝
―４―クロル―安息香酸2.9ｇを得た。Example 1 1.7 g of 4-chloroanthranilic acid and 1.5 g of o-phthalaldehydic acid were added to 50 ml of methanol and stirred at room temperature for 1 hour. Next, the solvent is concentrated, and the precipitated crystals are collected and dried to form colorless prismatic crystals of 2-
{[(o-carboxyphenyl)imino]methyl}
2.9 g of -4-chloro-benzoic acid was obtained.
この物質の融点、赤外吸収スペクトル、マスス
ペクトル及び元素分析値は次の通りであつた。 The melting point, infrared absorption spectrum, mass spectrum, and elemental analysis values of this substance were as follows.
融 点 257〜258℃
赤外吸収スペクトル νC＝ｏ（KBr）1730，
1687-1 cnνCN1500-1 cn
マススペクトル M+303
元素分析値 C15H10ClNO4
理 論 値 Ｃ：59.32 Ｈ：3.32 Ｎ：4.61
実 測 値 Ｃ：59.41 Ｈ：3.26 Ｎ：4.52
実施例 ２
５―メチルアントラニル酸1.5ｇとｏ―フタル
アルデヒド酸1.5ｇをエタノール40mlに加え室温
で１時間撹拌した。次いで溶媒を濃縮し、析出す
る結晶を取、乾燥すると無色プリズム晶の２―
｛〔（ｏ―カルボキシフエニル）イミノ〕メチル｝
―５―メチル―安息香酸2.7ｇを得た。 Melting point 257-258℃ Infrared absorption spectrum ν C = o (KBr) 1730,
1687 -1 cn ν C N1500 -1 cn Mass spectrum M + 303 Elemental analysis value C 15 H 10 ClNO 4 Theoretical value C: 59.32 H: 3.32 N: 4.61 Actual value C: 59.41 H: 3.26 N: 4.52 Example 2 1.5 g of 5-methylanthranilic acid and 1.5 g of o-phthalaldehydic acid were added to 40 ml of ethanol and stirred at room temperature for 1 hour. Next, the solvent is concentrated, and the precipitated crystals are collected and dried to form colorless prismatic crystals of 2-
{[(o-carboxyphenyl)imino]methyl}
2.7 g of -5-methyl-benzoic acid was obtained.
この物質の融点、赤外吸収スペクトル、マスス
ペクトル及び元素分析値は次の通りであつた。 The melting point, infrared absorption spectrum, mass spectrum, and elemental analysis values of this substance were as follows.
融 点 220〜221℃
赤外吸収スペクトル νC＝ｏ（KBr）1780，
1665-1 cnνCN1515-1 cn
マススペクトル M+283
元素分析値 C16H13NO4
理 論 値 Ｃ：67.84 Ｈ：4.63 Ｎ：4.95
実 測 値 Ｃ：67.78 Ｈ：4.70 Ｎ：4.87
以下、実施例２の方法に準じて下記の化合物を
合成した。 Melting point 220-221℃ Infrared absorption spectrum ν C = o (KBr) 1780,
1665 -1 cn ν C N1515 -1 cn Mass spectrum M + 283 Elemental analysis value C 16 H 13 NO 4 Theoretical value C: 67.84 H: 4.63 N: 4.95 Actual value C: 67.78 H: 4.70 N: 4.87 Below, The following compound was synthesized according to the method of Example 2.
２―｛〔（ｏ―カルボキシフエニル）イミノ〕メ
チル｝―４―ニトロ―安息香酸
融 点 271〜272℃
２―｛〔（ｏ―カルボキシフエニル）イミノ〕メ
チル｝―５―クロル―安息香酸
融 点 243〜245℃
２―｛〔（ｏ―カルボキシフエニル）イミノ〕メ
チル｝―５―ヨード―安息香酸
融 点 237〜239℃
２―｛〔（ｏ―カルボキシフエニル）イミノ〕メ
チル｝―４，５―ジメトキシ―安息香酸メチルエ
ステル
融 点 213〜214℃
２―｛〔（ｏ―カルボキシフエニル）イミノ〕メ
チル｝―安息香酸
融 点 230〜231℃
２―｛〔（ｏ―カルボキシフエニル）イミノ〕メ
チル｝―ニコチン酸エチルエステル
融 点 168〜170℃ 2-{[(o-carboxyphenyl)imino]methyl}-4-nitro-benzoic acid Melting point 271-272℃ 2-{[(o-carboxyphenyl)imino]methyl}-5-chloro-benzoic acid Melting point 243-245℃ 2-{[(o-carboxyphenyl)imino]methyl}-5-iodo-benzoic acid Melting point 237-239℃ 2-{[(o-carboxyphenyl)imino]methyl}- 4,5-Dimethoxy-benzoic acid methyl ester Melting point 213-214℃ 2-{[(o-carboxyphenyl)imino]methyl}-benzoic acid Melting point 230-231℃ 2-{[(o-carboxyphenyl) )Imino]methyl}-nicotinic acid ethyl ester Melting point 168-170℃
Claims (1)
２個置換したハロゲン原子、低級アルキル基、低
級アルコキシ基、ニトロ基を、ＸはCH又はＮ原
子を、R2は水素原子又は低級アルキル基を意味
する）で表わされる安息香酸誘導体。[Claims] 1. General formula (In the formula, R 1 is a hydrogen atom and 1 to
A benzoic acid derivative represented by a disubstituted halogen atom, a lower alkyl group, a lower alkoxy group, or a nitro group, where X is a CH or N atom, and R 2 is a hydrogen atom or a lower alkyl group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12752780A JPS5750952A (en) | 1980-09-10 | 1980-09-10 | Benzoic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12752780A JPS5750952A (en) | 1980-09-10 | 1980-09-10 | Benzoic acid derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5750952A JPS5750952A (en) | 1982-03-25 |
| JPS6312466B2 true JPS6312466B2 (en) | 1988-03-18 |
Family
ID=14962214
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12752780A Granted JPS5750952A (en) | 1980-09-10 | 1980-09-10 | Benzoic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5750952A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02133971U (en) * | 1989-04-14 | 1990-11-07 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2668770A1 (en) * | 1990-11-07 | 1992-05-07 | Nyco Sa | HETEROCYCLIC AMINO ACID ESTERS AND THEIR DERIVATIVES, AND THEIR APPLICATION AS ANTI-OXIDIZING ADDITIVES FOR HIGH TEMPERATURE LUBRICATING OILS. |
-
1980
- 1980-09-10 JP JP12752780A patent/JPS5750952A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02133971U (en) * | 1989-04-14 | 1990-11-07 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5750952A (en) | 1982-03-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR0146352B1 (en) | Processes for the preparation of morniflumate and analogous compounds | |
| JPS6312466B2 (en) | ||
| JP2005523324A (en) | Compounds useful for the preparation of camptothecin derivatives | |
| JPH0730046B2 (en) | Quinazoline acetic acid derivative | |
| JPH0144708B2 (en) | ||
| JPS6327337B2 (en) | ||
| JPH0159273B2 (en) | ||
| JPS6154016B2 (en) | ||
| JP2004217665A (en) | Process for preparation of 9-amino camptothecin | |
| JPH0378384B2 (en) | ||
| JPS5813550B2 (en) | Sinquinapiride (4,3-D) Pyrimidinedione | |
| JPS607623B2 (en) | 1-Carbamoyl-5-fluorouracil derivative and method for producing the same | |
| JPS609503B2 (en) | Tetrachlornaphthalic acid imide derivative and its production method | |
| JPS6020387B2 (en) | Method for producing novel quinazoline derivatives | |
| JP2997702B2 (en) | Method for producing styryl compound | |
| JPS5852995B2 (en) | Method for producing furfural derivatives | |
| JPS5888361A (en) | 3-amino-1,4-bis(alkoxycarbonyl)maleimide compound and its preparation | |
| JPS5942677B2 (en) | 100% free of charge | |
| JPS626543B2 (en) | ||
| SU1490115A1 (en) | Method of producing n-acetyl-2-chloro-3-iminoindoline hydrochloride | |
| JPS6148514B2 (en) | ||
| JP2717997B2 (en) | New hydrazone compound and process for producing triazole | |
| JPS5916879A (en) | Production of n-substituted imidazole | |
| JPS6231710B2 (en) | ||
| JP2001516741A (en) | Sulfo-N-hydroxysuccinimide and method for producing the same |