JPH027947B2 - - Google Patents
Info
- Publication number
- JPH027947B2 JPH027947B2 JP56107917A JP10791781A JPH027947B2 JP H027947 B2 JPH027947 B2 JP H027947B2 JP 56107917 A JP56107917 A JP 56107917A JP 10791781 A JP10791781 A JP 10791781A JP H027947 B2 JPH027947 B2 JP H027947B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- guanidinocaproic
- addition salt
- formula
- reaction
- 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 - Lifetime
Links
- 239000002253 acid Substances 0.000 claims description 8
- -1 guanidinocaproic acid p-ethoxycarbonyl phenyl ester Chemical class 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 claims description 5
- XUTCRESVECITBR-UHFFFAOYSA-N 2-(diaminomethylideneamino)hexanoic acid Chemical compound CCCCC(C(O)=O)N=C(N)N XUTCRESVECITBR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VTTGOBJSDGUBGO-UHFFFAOYSA-N 2-(diaminomethylideneamino)hexanoic acid;hydrochloride Chemical compound Cl.CCCCC(C(O)=O)N=C(N)N VTTGOBJSDGUBGO-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- RVPGGCLVLXPOHI-UHFFFAOYSA-N ethyl 4-[2-(diaminomethylideneamino)hexanoyloxy]benzoate Chemical compound CCCCC(NC(N)=N)C(=O)OC1=CC=C(C(=O)OCC)C=C1 RVPGGCLVLXPOHI-UHFFFAOYSA-N 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 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
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
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】
本発明は、グアニジノカプロン酸ｐ―エトキシ
カルボニルフエニルエステル又はその酸付加塩の
製法に係わるものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing guanidinocaproic acid p-ethoxycarbonylphenyl ester or an acid addition salt thereof.
本発明の方法は、グアニジノカプロン酸又はそ
の酸付加塩とｐ―ヒドロキシ安息香酸エチルエス
テルとを反応させるに際し、式（）
〔式中R1は低級アルキル基を、R2は水素原子、
又はメチル基を示す。Ｘはハロゲン原子を示す。〕
で示されるイミドハライドを使用することによ
り、遂げられるものである。 In the method of the present invention, when reacting guanidinocaproic acid or its acid addition salt with p-hydroxybenzoic acid ethyl ester, the formula () [In the formula, R 1 is a lower alkyl group, R 2 is a hydrogen atom,
Or represents a methyl group. X represents a halogen atom. ] This can be achieved by using the imide halide shown in the following.
ここにおいて用いられるイミドハライドはジメ
チルホルムアミド、ジメチルアセタミド、ジエチ
ルホルムアミドなどとクロル化剤、ブロム化剤、
例えば五塩化燐、三塩化燐、オキシ塩化燐、塩化
チオニル、オキザリルクロリド、ホスゲン、三臭
化燐などのハロゲン化剤とを反応させることによ
つて容易に得ることができる。 The imide halides used here include dimethylformamide, dimethylacetamide, diethylformamide, chlorination agents, bromination agents, etc.
For example, it can be easily obtained by reacting with a halogenating agent such as phosphorus pentachloride, phosphorus trichloride, phosphorus oxychloride, thionyl chloride, oxalyl chloride, phosgene, or phosphorus tribromide.
かくして得られるイミドハライドを、グアニジ
ノカプロン酸又はその酸付加塩とｐ―ヒドロキシ
安息香酸エチルエステルとの混合物中へ添加する
ことによつて反応を進めることができる。ここに
おいて用いられる溶媒としてはベンゼン、トルエ
ン、キシレン、ジオキサン、テトラヒドロフラ
ン、ヘキサン、ヘプタン、アセトニトリル、エチ
ルエーテルなど反応に関与しないものであればよ
い。またこれら溶媒はイミドハライドを調整する
ときにも使用できるものである。 The reaction can be carried out by adding the imidohalide thus obtained into a mixture of guanidinocaproic acid or its acid addition salt and p-hydroxybenzoic acid ethyl ester. The solvent used here may be one that does not participate in the reaction, such as benzene, toluene, xylene, dioxane, tetrahydrofuran, hexane, heptane, acetonitrile, and ethyl ether. These solvents can also be used when preparing imide halides.
時により、イミドハライドが結晶として調整中
に析出することがあるが、かゝる場合には、イミ
ドハライドを含む懸濁液の中へ原料化合物を添加
して反応を進めることもできる。 Occasionally, imidohalide may precipitate as crystals during preparation, but in such a case, the reaction may proceed by adding the raw material compound to the suspension containing imidohalide.
反応を好適に進めるためには、有機又は無機の
塩基を加えるとよい。かゝる場合に用いられる塩
基としては、トリエチルアミン、ジメチルアニリ
ン、ジエチルアニリン、ピリジンなど三級アミ
ン、炭酸ソーダ、重炭酸ソーダなどの炭酸塩があ
げられる。グアニジノカプロン酸を酸付加塩とし
て用いる場合における酸としては、塩酸、臭化水
素酸、沃化水素酸、硫酸、トルエンスルホン酸、
ベンゼンスルホン酸、メタンスルホン酸などがあ
げられる。 In order to proceed with the reaction suitably, it is preferable to add an organic or inorganic base. Bases used in such cases include tertiary amines such as triethylamine, dimethylaniline, diethylaniline, and pyridine, and carbonates such as sodium carbonate and sodium bicarbonate. Examples of acids when using guanidinocaproic acid as an acid addition salt include hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, toluenesulfonic acid,
Examples include benzenesulfonic acid and methanesulfonic acid.
また反応は室温乃至は稍々冷却下で進めること
ができる。反応時間は３〜４時間で充分である。 Further, the reaction can proceed at room temperature or under slight cooling. A reaction time of 3 to 4 hours is sufficient.
本発明によつて提供される化合物は酵素阻害作
用を有し医薬として有用な化合物である。 The compounds provided by the present invention have enzyme inhibitory activity and are useful as pharmaceuticals.
以下実施例を記述して本発明を更に具体的に説
明する。 The present invention will be explained in more detail by describing examples below.
実施例 １
アセトニトリル60ml中に、グアニジノカプロン
酸塩酸塩17.2ｇ、ｐ―ヒドロキシ安息香酸エチル
エステル16.3ｇ、ピリジン15.6ｇを加え撹拌し
た。これにアセトニトリル70ml中、ジメチルホル
ムアミド21.6ｇ、オキザリルクロリド12.5ｇとか
ら調整したクロロメチレンジメチルイミニユウム
クロリド溶液を室温で加え、更に同温度で４時間
撹拌反応した。Example 1 17.2 g of guanidinocaproic hydrochloride, 16.3 g of p-hydroxybenzoic acid ethyl ester, and 15.6 g of pyridine were added to 60 ml of acetonitrile and stirred. A chloromethylene dimethyl iminium chloride solution prepared from 21.6 g of dimethylformamide and 12.5 g of oxalyl chloride in 70 ml of acetonitrile was added to this at room temperature, and the reaction was further stirred at the same temperature for 4 hours.
減圧下で溶媒を溜去し、残渣に食塩水を加え分
離した油状物を取り、エチルエーテルで洗滌して
グアニジノカプロン酸ｐ―エトキシカルボニルフ
エニルエステル塩酸塩を淡黄色油状物として得
た。 The solvent was distilled off under reduced pressure, and brine was added to the residue to obtain a separated oil, which was washed with ethyl ether to obtain guanidinocaproic acid p-ethoxycarbonylphenyl ester hydrochloride as a pale yellow oil.
得量 21.0ｇ
実施例 ２
トルエン50mlにジメチルホルムアミド13.16ｇ
を加え10℃に冷却した。塩化チオニル7.14ｇを加
え30分撹拌した。 Yield: 21.0g Example 2: 13.16g of dimethylformamide in 50ml of toluene
was added and cooled to 10°C. 7.14 g of thionyl chloride was added and stirred for 30 minutes.
次いでグアニジノカプロン酸塩酸塩10.48ｇを
加え、更に、ｐ―ヒドロキシ安息香酸エチルエス
テル9.97ｇ、トリエチルアミン12.14ｇを加え室
温で３時間撹拌反応した。 Next, 10.48 g of guanidinocaproic acid hydrochloride was added, followed by 9.97 g of p-hydroxybenzoic acid ethyl ester and 12.14 g of triethylamine, and the reaction was stirred at room temperature for 3 hours.
減圧下溶媒を溜去し、残渣に食塩水を加え、分
離した油状物を取り、エチルエーテルで洗滌し
て、グアニジノカプロン酸ｐ―エトキシカルボニ
ルフエニルエステル塩酸塩を淡黄色油状物として
得た。 The solvent was distilled off under reduced pressure, brine was added to the residue, and the separated oil was taken and washed with ethyl ether to obtain guanidinocaproic acid p-ethoxycarbonylphenyl ester hydrochloride as a pale yellow oil.
得量 12.8ｇ Yield: 12.8g
Claims (1)
―ヒドロキシ安息香酸エチルエステルとを 式（） 〔式中R1は低級アルキル基を、R2は、水素原
子又はメチル基を、Ｘはハロゲン原子を示す。〕 で示されるイミドハライドの存在下反応させグア
ニジノカプロン酸ｐ―エトキシカルボニルフエニ
ルエステル又はその酸付加塩を得ることを特徴と
するグアニジノカプロン酸ｐ―エトキシカルボニ
ルフエニルエステル又はその酸付加塩の製造方
法。[Claims] 1. Guanidinocaproic acid or its acid addition salt and p
-Hydroxybenzoic acid ethyl ester and the formula () [In the formula, R 1 represents a lower alkyl group, R 2 represents a hydrogen atom or a methyl group, and X represents a halogen atom. ] Production of guanidinocaproic acid p-ethoxycarbonyl phenyl ester or its acid addition salt, which is characterized by reacting in the presence of an imidohalide represented by the formula to obtain guanidinocaproic acid p-ethoxycarbonyl phenyl ester or its acid addition salt. Method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56107917A JPS5810555A (en) | 1981-07-09 | 1981-07-09 | Preparation of guanidinocaproic acid p-ethoxycarbonylphenyl |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56107917A JPS5810555A (en) | 1981-07-09 | 1981-07-09 | Preparation of guanidinocaproic acid p-ethoxycarbonylphenyl |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5810555A JPS5810555A (en) | 1983-01-21 |
| JPH027947B2 true JPH027947B2 (en) | 1990-02-21 |
Family
ID=14471321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56107917A Granted JPS5810555A (en) | 1981-07-09 | 1981-07-09 | Preparation of guanidinocaproic acid p-ethoxycarbonylphenyl |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5810555A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104736000B (en) * | 2012-10-18 | 2018-07-06 | 日清食品控股株式会社 | Saline taste reinforcing agent and preparation method thereof and saline taste Enhancement Method |
-
1981
- 1981-07-09 JP JP56107917A patent/JPS5810555A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5810555A (en) | 1983-01-21 |
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