JP2016505009A5 - - Google Patents
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- Publication number
- JP2016505009A5 JP2016505009A5 JP2015552689A JP2015552689A JP2016505009A5 JP 2016505009 A5 JP2016505009 A5 JP 2016505009A5 JP 2015552689 A JP2015552689 A JP 2015552689A JP 2015552689 A JP2015552689 A JP 2015552689A JP 2016505009 A5 JP2016505009 A5 JP 2016505009A5
- Authority
- JP
- Japan
- Prior art keywords
- adenosyl
- methionine
- indole
- propionate
- disorders
- 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
- MEFKEPWMEQBLKI-AIRLBKTGSA-N S-adenosyl-L-methioninate Chemical compound 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 claims description 34
- GOLXRNDWAUTYKT-UHFFFAOYSA-M 3-(1H-indol-3-yl)propanoate Chemical compound C1=CC=C2C(CCC(=O)[O-])=CNC2=C1 GOLXRNDWAUTYKT-UHFFFAOYSA-M 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 241000124008 Mammalia Species 0.000 claims description 9
- 208000035475 disorder Diseases 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- VHPOFDUCFKOUHV-XKGORWRGSA-N (2s)-2-amino-4-[[(2s,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-methylsulfonio]butanoate;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.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 VHPOFDUCFKOUHV-XKGORWRGSA-N 0.000 claims description 6
- GOLXRNDWAUTYKT-UHFFFAOYSA-N 3-(1H-indol-3-yl)propanoic acid Chemical compound C1=CC=C2C(CCC(=O)O)=CNC2=C1 GOLXRNDWAUTYKT-UHFFFAOYSA-N 0.000 claims description 6
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 208000012659 Joint disease Diseases 0.000 claims description 4
- 208000012902 Nervous system disease Diseases 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 208000016247 Soft tissue disease Diseases 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 230000006378 damage Effects 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 208000027753 pain disease Diseases 0.000 claims description 4
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 239000003623 enhancer Substances 0.000 claims description 3
- 239000003290 indole 3-propionic acid Substances 0.000 claims description 3
- 208000019423 liver disease Diseases 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- XQMWYLXPEGFCFT-XKGORWRGSA-N (2s)-2-amino-4-[[(2s,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-methylsulfonio]butanoate;hydroiodide Chemical compound [I-].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 XQMWYLXPEGFCFT-XKGORWRGSA-N 0.000 claims description 2
- RFCNTHQSTXQCEP-UHFFFAOYSA-O (3-amino-3-carboxypropyl)-[[5-(6-aminopurin-9-yl)-4-hydroxy-3-(4-methylphenyl)sulfonyloxyoxolan-2-yl]methyl]-methylsulfanium Chemical group OC(=O)C(N)CC[S+](C)CC1OC(N2C3=NC=NC(N)=C3N=C2)C(O)C1OS(=O)(=O)C1=CC=C(C)C=C1 RFCNTHQSTXQCEP-UHFFFAOYSA-O 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 230000007067 DNA methylation Effects 0.000 claims description 2
- 208000026350 Inborn Genetic disease Diseases 0.000 claims description 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 208000025966 Neurological disease Diseases 0.000 claims description 2
- 208000028017 Psychotic disease Diseases 0.000 claims description 2
- 230000006093 RNA methylation Effects 0.000 claims description 2
- 208000027520 Somatoform disease Diseases 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
- 208000027418 Wounds and injury Diseases 0.000 claims description 2
- DYFPQIYEZQULMZ-XKGORWRGSA-N [(3s)-3-amino-3-carboxypropyl]-[[(2s,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-methylsulfanium;chloride Chemical compound [Cl-].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 DYFPQIYEZQULMZ-XKGORWRGSA-N 0.000 claims description 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 239000008280 blood Substances 0.000 claims description 2
- 210000004369 blood Anatomy 0.000 claims description 2
- 239000001273 butane Substances 0.000 claims description 2
- VERAMNDAEAQRGS-UHFFFAOYSA-N butane-1,4-disulfonic acid Chemical compound OS(=O)(=O)CCCCS(O)(=O)=O VERAMNDAEAQRGS-UHFFFAOYSA-N 0.000 claims description 2
- RIBDTNDXEMEVOG-UHFFFAOYSA-N butane-1,4-disulfonic acid;3-(1h-indol-3-yl)propanoic acid Chemical compound OS(=O)(=O)CCCCS(O)(=O)=O.C1=CC=C2C(CCC(=O)O)=CNC2=C1 RIBDTNDXEMEVOG-UHFFFAOYSA-N 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 210000003169 central nervous system Anatomy 0.000 claims description 2
- VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 208000016361 genetic disease Diseases 0.000 claims description 2
- 208000014674 injury Diseases 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 208000020016 psychiatric disease Diseases 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 2
- 210000001519 tissue Anatomy 0.000 claims description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 3
- 229920001661 Chitosan Polymers 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- LEUIUWYZAHKPSE-UHFFFAOYSA-L disodium;butane-1,4-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)CCCCS([O-])(=O)=O LEUIUWYZAHKPSE-UHFFFAOYSA-L 0.000 claims 1
- 229920001519 homopolymer Polymers 0.000 claims 1
- 210000000653 nervous system Anatomy 0.000 claims 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 206010029216 Nervousness Diseases 0.000 description 1
- RLGDNDVNTBSFKJ-UHFFFAOYSA-N OC(CCC1=CNC2=CC=CC=C12)=O.OC(CCC1=CNC2=CC=CC=C12)=O.OS(CCCCS(O)(=O)=O)(=O)=O Chemical compound OC(CCC1=CNC2=CC=CC=C12)=O.OC(CCC1=CNC2=CC=CC=C12)=O.OS(CCCCS(O)(=O)=O)(=O)=O RLGDNDVNTBSFKJ-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361753300P | 2013-01-16 | 2013-01-16 | |
| US61/753,300 | 2013-01-16 | ||
| US201361792467P | 2013-03-15 | 2013-03-15 | |
| US61/792,467 | 2013-03-15 | ||
| PCT/US2014/011935 WO2014113609A1 (en) | 2013-01-16 | 2014-01-16 | Stable indole-3-propionate salts of s-adenosyl-l-methionine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016505009A JP2016505009A (ja) | 2016-02-18 |
| JP2016505009A5 true JP2016505009A5 (enExample) | 2017-02-09 |
| JP6479681B2 JP6479681B2 (ja) | 2019-03-06 |
Family
ID=51210072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015552689A Active JP6479681B2 (ja) | 2013-01-16 | 2014-01-16 | 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 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9534010B2 (enExample) |
| EP (1) | EP2945959B1 (enExample) |
| JP (1) | JP6479681B2 (enExample) |
| KR (1) | KR102186066B1 (enExample) |
| CN (1) | CN105073767B (enExample) |
| ES (1) | ES2824807T3 (enExample) |
| WO (1) | WO2014113609A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT201700074957A1 (it) | 2017-07-04 | 2019-01-04 | Gnosis Spa | Sale di (ss)-adenosil metionina con inositolo esafosfato e procedimento per ottenerlo |
| US11324774B2 (en) * | 2018-01-05 | 2022-05-10 | Augusta University Research Institute, Inc. | Compositions of oral alkaline salts and metabolic acid inducers and uses thereof |
| JP2021046375A (ja) * | 2019-09-19 | 2021-03-25 | ポッカサッポロフード＆ビバレッジ株式会社 | β３アドレナリン受容体活性化剤 |
| CN117883439A (zh) * | 2024-01-18 | 2024-04-16 | 中国人民解放军陆军军医大学第一附属医院 | 吲哚-3-丙酸在制备抑制破骨细胞分化药物中的应用 |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2969353A (en) | 1957-02-06 | 1961-01-24 | Merck & Co Inc | Process for the preparation of "active methionine" and products obtained thereby |
| DE1803978C2 (de) | 1968-10-18 | 1985-05-02 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verfahren zur Gewinnung von S-Adenosyl-l-methionin und S-Adenosyl-l-ethionin |
| IE37913B1 (en) | 1972-08-02 | 1977-11-09 | Bioresearch Sas | Salt of s-adenosyl-l-methionine |
| US4028183A (en) | 1973-06-27 | 1977-06-07 | Bioresearch Limited | Process of preparing double salts of S-adenosyl-L-methionine |
| IE39517B1 (en) | 1973-06-27 | 1978-10-25 | Bioresearch Sas | Double salts of s-adenosyl-l-methhionine |
| AR221676A1 (es) | 1974-07-12 | 1981-03-13 | Bioresearch Sas | Procedimiento para la preparacion de sales estables sulfonicas y/o sulfuricas de la s-adenosil-l-metionina,particularmente utiles como donadores especificos de metilo para las reacciones bioquimicas de transferencia del grupo ch3;asi como tambien las reacciones fundamentales en el metabolismo lipilico,protilico y glucidico |
| DE2646269A1 (de) | 1975-10-16 | 1977-04-28 | Yamasa Shoyu Kk | Stabilisierte s-adenosyl-l-methionin- zubereitung und verfahren zur herstellung derselben |
| GB2001976B (en) | 1977-08-03 | 1982-03-10 | Yamasa Shoyu Kk | S-adenosyl-l-methionine compositions and production thereof |
| GB2064523B (en) | 1979-12-04 | 1983-06-29 | Kanegafuchi Chemical Ind | Stable composition of s-adenosyl-l-methionine |
| IT1137640B (it) | 1981-08-24 | 1986-09-10 | Bioresearch Srl | Sali stabili della s-adenosilmetionina,processo per la loro preparazione e composizioni terapeutiche che li comprendono come principio attivo |
| IT1137892B (it) | 1981-08-24 | 1986-09-10 | Bioresearch Srl | Sali stabili della s-adenosilmetionina,processo per la loro preparazione e composizioni terapeutiche che li comprendono come principio attivo |
| IT1139974B (it) | 1981-09-11 | 1986-09-24 | Bioresearch Srl | Derivati della s-adenosilmetionina,processo per la preparazione e composizioni terapeutiche che li contengono come principio attivo |
| IT1169774B (it) | 1983-08-24 | 1987-06-03 | Bioresearch Spa | Composizioni terapeutiche iniettabili contenenti sali stabili della s-adenosil-l-metionina |
| IT1173992B (it) | 1984-05-16 | 1987-06-24 | Bioresearch Spa | Sali stabili della solfo-adenosil-l-metionina (same) particolarmente idonei per uso farmaceutico orale |
| IT1173990B (it) | 1984-05-16 | 1987-06-24 | Bioresearch Spa | Sali stabili della solfo-adenosil-l-metionina (same) particolarmente adatti per uso parenterale |
| IT1200589B (it) | 1985-02-14 | 1989-01-27 | Gibipharma Spa | Derivati naturali attivita farmagologica |
| JPH03501970A (ja) | 1987-10-09 | 1991-05-09 | ザッピア ヴィンセンツォ | Ｓ‐アデノシル‐ｌ‐メチオニン（ｓａｍ）のアシル化タウリン誘導体との親油性塩 |
| JPH02290896A (ja) | 1989-04-28 | 1990-11-30 | Fuji Kagaku Kogyo Kk | 新規なｓ―アデノシルメチオニン誘導体 |
| DE19632823C1 (de) | 1996-08-14 | 1997-11-20 | Symbio Herborn Group Gmbh & Co | Komplexe zwischen S-(+)-Adenosylmethionin und 3'-Azido-2',3'-didesoxynucleosid als potente Inhibitoren der HIV-Replikation |
| IT1318535B1 (it) | 2000-05-25 | 2003-08-27 | Chementecno Srl | Processo per la preparazione di sali farmaceuticamente accettabili di(ss,rs)-s-adenosil-l-metionina. |
| KR20020088498A (ko) | 2001-05-17 | 2002-11-29 | (주)미토콘 | 에스-아데노실메티오닌을 유효성분으로 함유하는 인슐린저항증 개선용 조성물 |
| US6649753B2 (en) * | 2001-06-07 | 2003-11-18 | Orchid Chemicals & Pharmaceuticals Ltd. | Stable salts of S-adenosyl-L-methionine (SAMe) and the process for their preparation |
| US6881837B2 (en) | 2001-06-07 | 2005-04-19 | Orchid Chemicals & Pharmaceuticals Ltd. | Chemical synthesis of S-adenosyl-L-methionine with enrichment of (S,S)-isomer |
| US20040029830A1 (en) * | 2002-08-06 | 2004-02-12 | Hebert Rolland F. | Water-soluble indole-3-propionic acid |
| US20050272687A1 (en) * | 2004-06-08 | 2005-12-08 | Hebert Rolland F | Stable S-adenosyl-l-methionine |
| US20060127506A1 (en) * | 2004-12-10 | 2006-06-15 | Hebert Rolland F | Compositions of S-adenosyl-L-methionine |
| 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. |
| ITMI20071374A1 (it) * | 2007-07-10 | 2009-01-11 | Gnosis Spa | Sali stabili di s-adenosilmetionina e processo per il loro ottenimento. |
| WO2009018368A1 (en) * | 2007-07-30 | 2009-02-05 | Los Angeles Biomedical Research Institute At Harbor-Ucla Medical Center | Combination treatment of nmda (n-methyl-d-aspartate)-enhancer, glycine transporter inhibitor, d-amino acid oxidase inhibitor (daaoi) for neuropsychiatric disorders |
| US20100004191A1 (en) | 2008-07-01 | 2010-01-07 | Rolland F Hebert | Compositions of S-adenosyl-L-methionine. |
-
2014
- 2014-01-16 JP JP2015552689A patent/JP6479681B2/ja active Active
- 2014-01-16 US US14/760,067 patent/US9534010B2/en active Active
- 2014-01-16 ES ES14704211T patent/ES2824807T3/es active Active
- 2014-01-16 CN CN201480005105.4A patent/CN105073767B/zh active Active
- 2014-01-16 WO PCT/US2014/011935 patent/WO2014113609A1/en not_active Ceased
- 2014-01-16 EP EP14704211.3A patent/EP2945959B1/en active Active
- 2014-01-16 KR KR1020157021851A patent/KR102186066B1/ko not_active Expired - Fee Related
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