CA1240321A - Process for preparing 5,6,7,8-tetrahydro-6-(l-erythro- 1',2'-dihydroxypropyl)pterin - Google Patents
Process for preparing 5,6,7,8-tetrahydro-6-(l-erythro- 1',2'-dihydroxypropyl)pterinInfo
- Publication number
- CA1240321A CA1240321A CA000474602A CA474602A CA1240321A CA 1240321 A CA1240321 A CA 1240321A CA 000474602 A CA000474602 A CA 000474602A CA 474602 A CA474602 A CA 474602A CA 1240321 A CA1240321 A CA 1240321A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- alkali metal
- metal hydroxide
- hydroxide
- basic medium
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- HNXQXTQTPAJEJL-UHFFFAOYSA-N 2-aminopteridin-4-ol Chemical compound C1=CN=C2NC(N)=NC(=O)C2=N1 HNXQXTQTPAJEJL-UHFFFAOYSA-N 0.000 title claims description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 28
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000007864 aqueous solution Substances 0.000 claims description 23
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 10
- 229910003446 platinum oxide Inorganic materials 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 9
- 235000011181 potassium carbonates Nutrition 0.000 claims description 9
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- -1 alkali metal salt Chemical class 0.000 claims description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims description 4
- 229910052808 lithium carbonate Inorganic materials 0.000 claims description 4
- 229910003445 palladium oxide Inorganic materials 0.000 claims description 4
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 235000011056 potassium acetate Nutrition 0.000 claims description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 claims description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical group [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 claims description 2
- 239000011736 potassium bicarbonate Substances 0.000 claims description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 2
- 229940086066 potassium hydrogencarbonate Drugs 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- CZCSLHYZEQSUNV-UHFFFAOYSA-N [Na].OB(O)O Chemical compound [Na].OB(O)O CZCSLHYZEQSUNV-UHFFFAOYSA-N 0.000 claims 1
- AENYAMPVQFAKHY-UHFFFAOYSA-N boric acid;potassium Chemical compound [K].OB(O)O AENYAMPVQFAKHY-UHFFFAOYSA-N 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 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 abstract description 29
- 229960004617 sapropterin Drugs 0.000 abstract description 26
- 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 abstract description 19
- 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 abstract description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- 239000000706 filtrate Substances 0.000 description 21
- 239000006185 dispersion Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
- 238000004128 high performance liquid chromatography Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 238000005984 hydrogenation reaction Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 238000013019 agitation Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- FNKQXYHWGSIFBK-FKZODXBYSA-N (6s)-2-amino-6-[(1r,2s)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-1h-pteridin-4-one Chemical compound N1C(N)=NC(=O)C2=C1NC[C@@H]([C@@H](O)[C@@H](O)C)N2 FNKQXYHWGSIFBK-FKZODXBYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 201000011252 Phenylketonuria Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SJLOMQIUPFZJAN-UHFFFAOYSA-N oxorhodium Chemical compound [Rh]=O SJLOMQIUPFZJAN-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910003450 rhodium oxide Inorganic materials 0.000 description 1
- RKSUYBCOVNCALL-NTVURLEBSA-N sapropterin dihydrochloride Chemical compound Cl.Cl.N1=C(N)NC(=O)C2=C1NC[C@H]([C@@H](O)[C@@H](O)C)N2 RKSUYBCOVNCALL-NTVURLEBSA-N 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 229960004599 sodium borate Drugs 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical compound [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
- C07D475/02—Heterocyclic compounds containing pteridine ring systems with an oxygen atom directly attached in position 4
- C07D475/04—Heterocyclic compounds containing pteridine ring systems with an oxygen atom directly attached in position 4 with a nitrogen atom directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59033839A JPS60178887A (ja) | 1984-02-23 | 1984-02-23 | ５，６，７，８−テトラヒドロ−ｌ−ビオプテリンの製造法 |
| JP33839/1984 | 1984-02-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1240321A true CA1240321A (en) | 1988-08-09 |
Family
ID=12397654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000474602A Expired CA1240321A (en) | 1984-02-23 | 1985-02-19 | Process for preparing 5,6,7,8-tetrahydro-6-(l-erythro- 1',2'-dihydroxypropyl)pterin |
Country Status (7)
Families Citing this family (30)
| 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 |
| JPS60199889A (ja) * | 1984-03-24 | 1985-10-09 | Kanegafuchi Chem Ind Co Ltd | ５，６，７，８−テトラヒドロ−ｌ−エリスロ−ビオプテリンの硫酸塩およびその製法 |
| JPS60204786A (ja) * | 1984-03-29 | 1985-10-16 | Univ Nagoya | （６ｒ）―テトラヒドロビオプテリンの合成法 |
| US4665176A (en) * | 1984-10-23 | 1987-05-12 | Mitsui Toatsu Chemicals, Incorporated | Process for the preparation of 5,6,7,8-tetrahydrofolic acid |
| CA1262347A (en) * | 1985-01-28 | 1989-10-17 | Suntory Limited | Preparation process of (6r)-tetrahydro-l-biopterin |
| US4937342A (en) * | 1987-11-30 | 1990-06-26 | Kabushiki Kaisha Vitamin Kenkyusyo | Intermediates for synthesizing BH4 and its derivatives |
| US6162914A (en) * | 1998-04-24 | 2000-12-19 | Cerbios-Pharma S.A. | Process for the reduction of pterins |
| CH694251A5 (de) * | 1999-07-14 | 2004-10-15 | Eprova Ag | Herstellung von Tetrahydropterin und Derivaten. |
| ATE426021T1 (de) * | 2000-08-31 | 2009-04-15 | Asubio Pharma Co Ltd | Verfahren zur herstellung von biopterinen |
| US7442372B2 (en) | 2003-08-29 | 2008-10-28 | Biomarin Pharmaceutical Inc. | Delivery of therapeutic compounds to the brain and other tissues |
| EP3977999A1 (en) | 2003-11-17 | 2022-04-06 | BioMarin Pharmaceutical Inc. | Treatment of phenylketonuria with bh4 |
| ES2755334T3 (es) * | 2003-11-17 | 2020-04-22 | Merck & Cie | Proceso para la preparación de formas cristalinas B de clorhidrato de (6R)-L-eritro-tetrahidrobiopterina a partir de otras formas cristalinas |
| JP2008504295A (ja) * | 2004-06-25 | 2008-02-14 | ボード オブ リージェンツ， ザ ユニバーシティ オブ テキサス システム | 注意欠陥多動性障害及び高フェニルアラニン血症の治療のための方法及び組成物 |
| BRPI0517088A (pt) | 2004-11-17 | 2008-09-30 | Biomarin Pharm Inc | formulação de comprimido estável |
| EP1819340A2 (en) * | 2004-12-08 | 2007-08-22 | Biomarin Pharmaceutical Inc. | Methods and compositions for the treatment of pulmonary hypertension of the newborn |
| ES2317529T3 (es) | 2005-04-14 | 2009-04-16 | Shiratori Pharmaceutical Co., Ltd. | Metodo para producir cristales de forma alfa de hidrocloruro de sapropterina. |
| CA2631740A1 (en) * | 2005-12-05 | 2007-06-14 | Biomarin Pharmaceutical Inc. | Methods and compositions for the treatment of disease |
| CA2675134A1 (en) * | 2007-01-12 | 2008-07-24 | Biomarin Pharmaceutical Inc. | Pterin analogs |
| WO2008089148A1 (en) * | 2007-01-12 | 2008-07-24 | Biomarin Pharmaceutical Inc. | Method of treating a metabolic or neuropsychiatry disorder with a bh4 derivative prodrug |
| RU2486899C2 (ru) | 2007-04-11 | 2013-07-10 | Байомарин Фармасьютикал Инк. | Композиции тетрагидробиоптерина и способы его количественной оценки |
| CA2711160A1 (en) | 2008-01-03 | 2009-07-16 | Biomarin Pharmaceutical Inc. | Pterin analog for treating bh4 responsive condition |
| AR070109A1 (es) * | 2008-01-07 | 2010-03-17 | Biomarin Pharm Inc | Metodo para sintetizar tetrahidobiopterina |
| CN102443006B (zh) | 2010-10-13 | 2016-02-24 | 因华生技制药股份有限公司 | (6r)-四氢生物喋呤盐酸盐的制备方法 |
| TWI481612B (zh) * | 2010-10-15 | 2015-04-21 | Innopharmax Inc | （６ｒ）－四氫生物喋呤鹽酸鹽的製備方法 |
| US9216178B2 (en) | 2011-11-02 | 2015-12-22 | Biomarin Pharmaceutical Inc. | Dry blend formulation of tetrahydrobiopterin |
| CN102633799B (zh) | 2012-04-10 | 2014-06-25 | 凯莱英医药集团（天津）股份有限公司 | 一种从消旋体中间体拆分路线合成二盐酸沙丙蝶呤的方法 |
| CN102627644B (zh) | 2012-04-10 | 2014-04-16 | 凯莱英医药集团（天津）股份有限公司 | 一种通过直接手性合成方法制备二盐酸沙丙蝶呤的方法 |
| WO2016189542A1 (en) | 2015-05-28 | 2016-12-01 | Natco Pharma Ltd | Novel process for the preparation of sapropterin dihydrochloride and its key intermediate, l-biopterin |
| WO2019175328A1 (en) | 2018-03-14 | 2019-09-19 | Imba - Institut Für Molekulare Biotechnologie Gmbh | Bh4pathwayactivationandusethereoffortreatingcancer |
| WO2019175332A1 (en) | 2018-03-14 | 2019-09-19 | Imba - Institut Für Molekulare Biotechnologie Gmbh | Bh4 pathway inhibition and use thereof for treating t-cell mediated autoimmune diseases or hypersensitivity |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2741608A (en) * | 1951-03-08 | 1956-04-10 | Research Corp | 5-formyl-5,6,7,8-tetrahydropteroic acid and amides thereof and method of preparing same |
| JPS5883691A (ja) * | 1981-11-13 | 1983-05-19 | Kanegafuchi Chem Ind Co Ltd | １′，２′−ジアシル−（６ｒ，ｓ）−５，６，７，８−テトラヒドロ−ｌ−ビオプテリンおよびその製法 |
| 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 |
| JPS61172876A (ja) * | 1985-01-28 | 1986-08-04 | Shiratori Seiyaku Kk | （６ｒ）−テトラヒドロ−ｌ−バイオプテリンの製造法 |
| JPS61172877A (ja) * | 1985-01-28 | 1986-08-04 | Shiratori Seiyaku Kk | （６ｒ）−テトラヒドロ−ｌ−バイオプテリンの製造方法 |
-
1984
- 1984-02-23 JP JP59033839A patent/JPS60178887A/ja active Granted
-
1985
- 1985-02-19 CA CA000474602A patent/CA1240321A/en not_active Expired
- 1985-02-21 DE DE8585101861T patent/DE3573426D1/de not_active Expired
- 1985-02-21 AT AT85101861T patent/ATE46906T1/de not_active IP Right Cessation
- 1985-02-21 US US06/703,976 patent/US4595752A/en not_active Expired - Lifetime
- 1985-02-21 EP EP85101861A patent/EP0153696B1/en not_active Expired
- 1985-02-22 ES ES540638A patent/ES8601993A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US4595752A (en) | 1986-06-17 |
| ATE46906T1 (de) | 1989-10-15 |
| EP0153696B1 (en) | 1989-10-04 |
| JPH0212475B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-03-20 |
| EP0153696A2 (en) | 1985-09-04 |
| ES540638A0 (es) | 1985-11-16 |
| EP0153696A3 (en) | 1987-08-19 |
| JPS60178887A (ja) | 1985-09-12 |
| ES8601993A1 (es) | 1985-11-16 |
| DE3573426D1 (en) | 1989-11-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20050809 |