JPS61172877A - （６ｒ）−テトラヒドロ−ｌ−バイオプテリンの製造方法 - Google Patents
（６ｒ）−テトラヒドロ−ｌ−バイオプテリンの製造方法Info
- Publication number
- JPS61172877A JPS61172877A JP60012478A JP1247885A JPS61172877A JP S61172877 A JPS61172877 A JP S61172877A JP 60012478 A JP60012478 A JP 60012478A JP 1247885 A JP1247885 A JP 1247885A JP S61172877 A JPS61172877 A JP S61172877A
- Authority
- JP
- Japan
- Prior art keywords
- platinum
- based catalyst
- biopterin
- amine
- acyl
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- 125000002252 acyl group Chemical group 0.000 claims abstract description 14
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 14
- LHQIJBMDNUYRAM-UHFFFAOYSA-N L-erythro-Biopterin Natural products N1=C(N)NC(=O)C2=NC(C(O)C(O)C)=CN=C21 LHQIJBMDNUYRAM-UHFFFAOYSA-N 0.000 claims abstract description 12
- LHQIJBMDNUYRAM-DZSWIPIPSA-N L-erythro-biopterin Chemical compound N1=C(N)NC(=O)C2=NC([C@@H](O)[C@@H](O)C)=CN=C21 LHQIJBMDNUYRAM-DZSWIPIPSA-N 0.000 claims abstract description 11
- 150000001412 amines Chemical class 0.000 claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 8
- 238000011914 asymmetric synthesis Methods 0.000 abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 abstract description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract description 4
- -1 L-erythro- biopterin compound Chemical class 0.000 abstract description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract description 3
- 238000010531 catalytic reduction reaction Methods 0.000 abstract description 3
- 239000005515 coenzyme Substances 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract description 3
- 102000000632 Aromatic amino acid hydroxylases Human genes 0.000 abstract description 2
- 108050008079 Aromatic amino acid hydroxylases Proteins 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 108010069013 Phenylalanine Hydroxylase Proteins 0.000 abstract description 2
- 102100038223 Phenylalanine-4-hydroxylase Human genes 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 239000001257 hydrogen Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910019020 PtO2 Inorganic materials 0.000 abstract 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 229910003446 platinum oxide Inorganic materials 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- FNKQXYHWGSIFBK-RPDRRWSUSA-N sapropterin Chemical compound N1=C(N)NC(=O)C2=C1NC[C@H]([C@@H](O)[C@@H](O)C)N2 FNKQXYHWGSIFBK-RPDRRWSUSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000003211 malignant effect Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 2
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 206010060860 Neurological symptom Diseases 0.000 description 1
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000002651 drug therapy Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000006371 metabolic abnormality Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 230000002747 voluntary effect Effects 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
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60012478A JPS61172877A (ja) | 1985-01-28 | 1985-01-28 | （６ｒ）−テトラヒドロ−ｌ−バイオプテリンの製造方法 |
| US06/824,288 US4713454A (en) | 1985-01-28 | 1986-01-23 | Preparation process of (6R)-tetrahydro-L-biopterin |
| CA000500218A CA1262347A (en) | 1985-01-28 | 1986-01-23 | Preparation process of (6r)-tetrahydro-l-biopterin |
| EP86100944A EP0191335B1 (en) | 1985-01-28 | 1986-01-24 | Preparation process of (6r)-tetrahydro-l-biopterin |
| AT86100944T ATE66229T1 (de) | 1985-01-28 | 1986-01-24 | Verfahren zur herstellung von (6r)-tetrahydro-l- biopterin. |
| DE8686100944T DE3680800D1 (de) | 1985-01-28 | 1986-01-24 | Verfahren zur herstellung von (6r)-tetrahydro-l-biopterin. |
| AU52720/86A AU581052B2 (en) | 1985-01-28 | 1986-01-24 | Preparation process of (6R)-tetrahydro-L-biopterin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60012478A JPS61172877A (ja) | 1985-01-28 | 1985-01-28 | （６ｒ）−テトラヒドロ−ｌ−バイオプテリンの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61172877A true JPS61172877A (ja) | 1986-08-04 |
| JPH0586393B2 JPH0586393B2 (enrdf_load_stackoverflow) | 1993-12-10 |
Family
ID=11806488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60012478A Granted JPS61172877A (ja) | 1985-01-28 | 1985-01-28 | （６ｒ）−テトラヒドロ−ｌ−バイオプテリンの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61172877A (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60178887A (ja) * | 1984-02-23 | 1985-09-12 | Kanegafuchi Chem Ind Co Ltd | ５，６，７，８−テトラヒドロ−ｌ−ビオプテリンの製造法 |
| JP2007536210A (ja) * | 2003-11-17 | 2007-12-13 | メルック・エプロバ・アクチエンゲゼルシヤフト | （６ｒ）−ｌ−エリスロ−テトラヒドロビオプテリンジヒドロクロライドの結晶形 |
| JP2008520574A (ja) * | 2004-11-17 | 2008-06-19 | バイオマリン ファーマシューティカル インコーポレイテッド | テトラヒドロビオプテリンの安定性錠剤処方物 |
| WO2013168693A1 (ja) * | 2012-05-07 | 2013-11-14 | 白鳥製薬株式会社 | セピアプテリン及びテトラヒドロラクトイルプテリンの製造法 |
| WO2017138588A1 (ja) * | 2016-02-10 | 2017-08-17 | 住友化学株式会社 | １－メチルピロリジン－３－オールの製造方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60142959A (ja) * | 1983-12-28 | 1985-07-29 | Otsuka Pharmaceut Co Ltd | キノリン誘導体 |
-
1985
- 1985-01-28 JP JP60012478A patent/JPS61172877A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60142959A (ja) * | 1983-12-28 | 1985-07-29 | Otsuka Pharmaceut Co Ltd | キノリン誘導体 |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60178887A (ja) * | 1984-02-23 | 1985-09-12 | Kanegafuchi Chem Ind Co Ltd | ５，６，７，８−テトラヒドロ−ｌ−ビオプテリンの製造法 |
| JP2007536210A (ja) * | 2003-11-17 | 2007-12-13 | メルック・エプロバ・アクチエンゲゼルシヤフト | （６ｒ）−ｌ−エリスロ−テトラヒドロビオプテリンジヒドロクロライドの結晶形 |
| JP2011162568A (ja) * | 2003-11-17 | 2011-08-25 | Merck Eprova Ag | （６ｒ）−ｌ−エリスロ−テトラヒドロビオプテリンジヒドロクロライドの結晶形 |
| JP2008520574A (ja) * | 2004-11-17 | 2008-06-19 | バイオマリン ファーマシューティカル インコーポレイテッド | テトラヒドロビオプテリンの安定性錠剤処方物 |
| JP2014012740A (ja) * | 2004-11-17 | 2014-01-23 | Biomarin Pharmaceutical Inc | テトラヒドロビオプテリンの安定性錠剤処方物 |
| WO2013168693A1 (ja) * | 2012-05-07 | 2013-11-14 | 白鳥製薬株式会社 | セピアプテリン及びテトラヒドロラクトイルプテリンの製造法 |
| US9181254B2 (en) | 2012-05-07 | 2015-11-10 | Shiratori Pharmaceutical Co., Ltd. | Method for producing sepiapterin and tetrahydrolactoylpterin |
| JPWO2013168693A1 (ja) * | 2012-05-07 | 2016-01-07 | 白鳥製薬株式会社 | セピアプテリン及びテトラヒドロラクトイルプテリンの製造法 |
| WO2017138588A1 (ja) * | 2016-02-10 | 2017-08-17 | 住友化学株式会社 | １－メチルピロリジン－３－オールの製造方法 |
| US11084787B2 (en) | 2016-02-10 | 2021-08-10 | Sumitomo Chemical Company Limited | Method for producing 1-methylpyrrolidin-3-ol |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0586393B2 (enrdf_load_stackoverflow) | 1993-12-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |