DE60101575T2 - Verfahren zur herstellung von pharmazeutisch annehmbaren salzen des (ss,rs)-s-adenosyl-l-menthionin - Google Patents
Verfahren zur herstellung von pharmazeutisch annehmbaren salzen des (ss,rs)-s-adenosyl-l-menthionin Download PDFInfo
- Publication number
- DE60101575T2 DE60101575T2 DE60101575T DE60101575T DE60101575T2 DE 60101575 T2 DE60101575 T2 DE 60101575T2 DE 60101575 T DE60101575 T DE 60101575T DE 60101575 T DE60101575 T DE 60101575T DE 60101575 T2 DE60101575 T2 DE 60101575T2
- Authority
- DE
- Germany
- Prior art keywords
- same
- pharmaceutically acceptable
- adenosyl
- acid
- yeast
- 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
- 238000004519 manufacturing process Methods 0.000 title description 5
- 238000000034 method Methods 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- 229920005989 resin Polymers 0.000 claims description 13
- 239000011347 resin Substances 0.000 claims description 13
- 239000006166 lysate Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 238000001471 micro-filtration Methods 0.000 claims description 6
- 238000001223 reverse osmosis Methods 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 238000004042 decolorization Methods 0.000 claims description 2
- MEFKEPWMEQBLKI-AIRLBKTGSA-N S-adenosyl-L-methioninate Chemical class O[C@@H]1[C@H](O)[C@@H](C[S+](CC[C@H](N)C([O-])=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MEFKEPWMEQBLKI-AIRLBKTGSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241000235646 Cyberlindnera jadinii Species 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 230000009089 cytolysis Effects 0.000 description 4
- VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001123227 Saccharomyces pastorianus Species 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000000855 fermentation Methods 0.000 description 3
- 230000004151 fermentation Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000004470 DL Methionine Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000003534 Saccharomyces carlsbergensis Nutrition 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- FFEARJCKVFRZRR-UHFFFAOYSA-N methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 2
- 229930182817 methionine Natural products 0.000 description 2
- 235000006109 methionine Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000006340 racemization Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical group C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- XHJLCRULHISREH-UHFFFAOYSA-N 4-methylbenzenesulfonic acid;sulfo hydrogen sulfate Chemical compound OS(=O)(=O)OS(O)(=O)=O.CC1=CC=C(S(O)(=O)=O)C=C1 XHJLCRULHISREH-UHFFFAOYSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 206010008909 Chronic Hepatitis Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 241000775010 Saccharomyces pastorianus CBS 1513 Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- AXZAYXJCENRGIM-UHFFFAOYSA-J dipotassium;tetrabromoplatinum(2-) Chemical compound [K+].[K+].[Br-].[Br-].[Br-].[Br-].[Pt+2] AXZAYXJCENRGIM-UHFFFAOYSA-J 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 229910001487 potassium perchlorate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000005253 yeast cell Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/26—Preparation of nitrogen-containing carbohydrates
- C12P19/28—N-glycosides
- C12P19/38—Nucleosides
- C12P19/40—Nucleosides having a condensed ring system containing a six-membered ring having two nitrogen atoms in the same ring, e.g. purine nucleosides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2000MI001158A IT1318535B1 (it) | 2000-05-25 | 2000-05-25 | Processo per la preparazione di sali farmaceuticamente accettabili di(ss,rs)-s-adenosil-l-metionina. |
| ITMI001158 | 2000-05-25 | ||
| PCT/EP2001/003633 WO2001090130A1 (en) | 2000-05-25 | 2001-03-30 | Process for the preparation of pharmaceutically acceptable salts of (ss-rs)-s-adenosyl-l-methionine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60101575D1 DE60101575D1 (de) | 2004-01-29 |
| DE60101575T2 true DE60101575T2 (de) | 2004-06-03 |
Family
ID=11445118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60101575T Expired - Lifetime DE60101575T2 (de) | 2000-05-25 | 2001-03-30 | Verfahren zur herstellung von pharmazeutisch annehmbaren salzen des (ss,rs)-s-adenosyl-l-menthionin |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US20020010147A1 (enExample) |
| EP (1) | EP1283845B1 (enExample) |
| JP (1) | JP4777588B2 (enExample) |
| KR (1) | KR100737193B1 (enExample) |
| AT (1) | ATE256695T1 (enExample) |
| AU (2) | AU6584801A (enExample) |
| CA (1) | CA2407559C (enExample) |
| DE (1) | DE60101575T2 (enExample) |
| DK (1) | DK1283845T3 (enExample) |
| ES (1) | ES2208610T3 (enExample) |
| IT (1) | IT1318535B1 (enExample) |
| PT (1) | PT1283845E (enExample) |
| TR (1) | TR200302297T4 (enExample) |
| WO (1) | WO2001090130A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7033815B2 (en) | 2001-03-30 | 2006-04-25 | Board Of Regents, The University Of Texas System | Biosynthesis of S-adenosylmethionine in a recombinant yeast strain |
| CN100398659C (zh) * | 2002-09-16 | 2008-07-02 | 上海青瑞生物医药技术有限公司 | 旋光纯(s,s)-腺甘甲硫氨酸制备的方法 |
| US20050272687A1 (en) * | 2004-06-08 | 2005-12-08 | Hebert Rolland F | Stable S-adenosyl-l-methionine |
| US20090012036A1 (en) * | 2005-05-24 | 2009-01-08 | Hebert Rolland F | Stable S-adenosyl-L-methionine |
| ES2406412T3 (es) * | 2005-06-09 | 2013-06-06 | Gnosis S.P.A. | Células de Saccharomyces cerevisiae secas, liofilizadas y/o microencapsuladas con un alto contenido de (S)-(+)-S-adenosil-metionina |
| ITRM20050344A1 (it) * | 2005-06-30 | 2007-01-01 | Luca Maria De | Sali o complessi di sostanze metil-donatrici con acido fitico o suoi derivati e relativo metodo di sintesi. |
| CN1955306B (zh) * | 2005-10-28 | 2011-03-16 | 上海医药工业研究院 | 酵母菌生物合成、生产旋光纯腺苷甲硫氨酸的方法及其培养液 |
| ITMI20060629A1 (it) | 2006-03-31 | 2007-10-01 | Daniele Giovannone | Composizioni solide orali a base di s-adenosilmetionina e processo per il loro ottenimento |
| KR101070494B1 (ko) | 2006-05-10 | 2011-10-05 | 미쓰비시 타나베 파마 코퍼레이션 | Ｓ-아데노실-ｌ-메티오닌 함유 건조 효모의 제조방법 및 경구 섭취용 조성물 |
| US20070265211A1 (en) * | 2006-05-12 | 2007-11-15 | Matthias Rath | Novel composition and method effective in inhibiting the atherogenic process |
| ITMI20071374A1 (it) * | 2007-07-10 | 2009-01-11 | Gnosis Spa | Sali stabili di s-adenosilmetionina e processo per il loro ottenimento. |
| US20100004191A1 (en) * | 2008-07-01 | 2010-01-07 | Rolland F Hebert | Compositions of S-adenosyl-L-methionine. |
| JP6479681B2 (ja) | 2013-01-16 | 2019-03-06 | ヘーベルト サム−イー エルエルシー | Ｓ−アデノシル−ｌ−メチオニンの安定なインドール−３−プロピオネート塩 |
| ITMI20130426A1 (it) * | 2013-03-20 | 2014-09-21 | Gnosis Spa | S-adenosilmetionina sterile ad alto contenuto di isomero attivo per soluzioni iniettabili e procedimento per ottenerla |
| CN106349311B (zh) * | 2016-08-23 | 2018-04-13 | 北京金阳利康医药有限公司 | 从酵母发酵液中提取s‑腺苷蛋氨酸的方法 |
| IT201700074957A1 (it) | 2017-07-04 | 2019-01-04 | Gnosis Spa | Sale di (ss)-adenosil metionina con inositolo esafosfato e procedimento per ottenerlo |
| CN110396120B (zh) * | 2019-02-13 | 2020-05-12 | 山东惠仕莱生物科技有限公司 | 一种从s-腺苷蛋氨酸发酵液中提取分离s-腺苷蛋氨酸的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE39517B1 (en) * | 1973-06-27 | 1978-10-25 | Bioresearch Sas | Double salts of s-adenosyl-l-methhionine |
| JPS56145299A (en) * | 1980-04-11 | 1981-11-11 | Kanegafuchi Chem Ind Co Ltd | Purification of s-adenosyl-l-methionine |
| JPS5929700A (ja) * | 1982-08-13 | 1984-02-16 | Nippon Zeon Co Ltd | Ｓ−アデノシル−ｌ−メチオニンの精製法 |
| IT1169773B (it) * | 1983-08-24 | 1987-06-03 | Bioresearch Spa | Processo per la produzione di sali stabili della solfo-adenosil-l-metionina |
| IT1173990B (it) * | 1984-05-16 | 1987-06-24 | Bioresearch Spa | Sali stabili della solfo-adenosil-l-metionina (same) particolarmente adatti per uso parenterale |
-
2000
- 2000-05-25 IT IT2000MI001158A patent/IT1318535B1/it active
-
2001
- 2001-03-30 ES ES01943206T patent/ES2208610T3/es not_active Expired - Lifetime
- 2001-03-30 PT PT01943206T patent/PT1283845E/pt unknown
- 2001-03-30 AT AT01943206T patent/ATE256695T1/de active
- 2001-03-30 DE DE60101575T patent/DE60101575T2/de not_active Expired - Lifetime
- 2001-03-30 KR KR1020027015667A patent/KR100737193B1/ko not_active Expired - Lifetime
- 2001-03-30 EP EP01943206A patent/EP1283845B1/en not_active Expired - Lifetime
- 2001-03-30 WO PCT/EP2001/003633 patent/WO2001090130A1/en not_active Ceased
- 2001-03-30 JP JP2001586317A patent/JP4777588B2/ja not_active Expired - Lifetime
- 2001-03-30 DK DK01943206T patent/DK1283845T3/da active
- 2001-03-30 AU AU6584801A patent/AU6584801A/xx active Pending
- 2001-03-30 CA CA002407559A patent/CA2407559C/en not_active Expired - Lifetime
- 2001-03-30 AU AU2001265848A patent/AU2001265848B8/en not_active Expired
- 2001-03-30 TR TR2003/02297T patent/TR200302297T4/xx unknown
- 2001-04-11 US US09/829,906 patent/US20020010147A1/en not_active Abandoned
-
2002
- 2002-05-13 US US10/142,876 patent/US6958233B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2407559C (en) | 2009-12-22 |
| AU2001265848B8 (en) | 2006-05-04 |
| US6958233B2 (en) | 2005-10-25 |
| PT1283845E (pt) | 2004-04-30 |
| AU6584801A (en) | 2001-12-03 |
| EP1283845A1 (en) | 2003-02-19 |
| KR20030036183A (ko) | 2003-05-09 |
| ITMI20001158A0 (it) | 2000-05-25 |
| ITMI20001158A1 (it) | 2001-11-25 |
| TR200302297T4 (tr) | 2004-02-23 |
| US20020173012A1 (en) | 2002-11-21 |
| ATE256695T1 (de) | 2004-01-15 |
| AU2001265848B2 (en) | 2006-03-23 |
| JP4777588B2 (ja) | 2011-09-21 |
| IT1318535B1 (it) | 2003-08-27 |
| DK1283845T3 (da) | 2004-04-13 |
| KR100737193B1 (ko) | 2007-07-10 |
| EP1283845B1 (en) | 2003-12-17 |
| DE60101575D1 (de) | 2004-01-29 |
| WO2001090130A1 (en) | 2001-11-29 |
| CA2407559A1 (en) | 2001-11-29 |
| US20020010147A1 (en) | 2002-01-24 |
| ES2208610T3 (es) | 2004-06-16 |
| JP2003534349A (ja) | 2003-11-18 |
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