DK2625163T3 - Fremgangsmåde til fremstillingen af (3s,3s') 4,4'-disulfandiylbis (3-aminobutan 1- sulfonsyre) - Google Patents
Fremgangsmåde til fremstillingen af (3s,3s') 4,4'-disulfandiylbis (3-aminobutan 1- sulfonsyre) Download PDFInfo
- Publication number
- DK2625163T3 DK2625163T3 DK11769843.1T DK11769843T DK2625163T3 DK 2625163 T3 DK2625163 T3 DK 2625163T3 DK 11769843 T DK11769843 T DK 11769843T DK 2625163 T3 DK2625163 T3 DK 2625163T3
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- DK
- Denmark
- Prior art keywords
- temperature
- reacting
- benzyloxycarbonylamino
- give
- ethanol
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
- C07C323/66—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfo, esterified sulfo or halosulfonyl groups, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
- C07C319/24—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides by reactions involving the formation of sulfur-to-sulfur bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
- C07C321/14—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (15)
1. Fremgangsmåde til fremstilling af (3S,3S') 4,4'-disulfandiylbis(3-aminobutan 1-sulfonsyre) fra (S) ethyl 2-(benzyloxycarbonylamino) 4-(neopentyloxysulfonyl)butanoat A omfattende trinnene: (a) at reducere ethylesteren af A for at give (S) neopentyl 3-(benzyloxycarbonylamino) 4-hydroxybutan 1-sulfonat B; (b) at reagere alkoholen B med methansulfonanhydrid eller methansulfonylchlorid i tilstedeværelse af en base for at give (S) neopentyl 3-(benzyloxycarbonylamino) 4-(methylsulfonyloxy)butan 1-sulfonat C; (c) at reagere den mesylerede alkohol C med kaliumthioacetat for at give (S) 2-(benzyloxycarbonylamino) 4-(neopentyloxysulfonyl)butylthioacetat D; (d) at dimerisere D for at give (3S,3S') neopentyl 4,4'-disulfandiylbis(3-(benzyloxycarbonylamino)butan 1-sulfonat) E; og (e) at afbeskytte sulfonester og amingrupper af E ved omrøring af E i en refluksblanding af trifluoreddikesyre (TFA) og anisol, for at give (3S,3S') 4,4'-disulfandiylbis(3-aminobutan 1-sulfonsyre).
2. Fremgangsmåden ifølge krav 1, hvor trin (a) udføres ved at reagere A med et reduktionsmiddel-solvent-par valgt fra NaBHU/LiCI - blanding af tetrahydrofuran (THF) og ethanol og UBH4 - THF, ved en temperatur fra 0 °C til 25 °C, eller fortrinsvis trin (a) udføres ved at reagere A med UBH4 - THF ved en temperatur fra 20 °C til 25 °C.
3. Fremgangsmåden ifølge et hvilket som helst af kravene 1 til 2, hvor trin (b) udføres i tilstedeværelse af triethylamin som base, i et solvent valgt fra chloroform og en blanding af methyltert-butylether (MTBE) og toluen, ved en temperatur fra -10 °C til 10 °C.
4. Fremgangsmåden ifølge krav 1, hvor trin (b) udføres ved at reagere B med methansulfonylchlorid, i tilstedeværelse af triethylamin som base, i en blanding af MTBE og toluen i 3:2 volumenforhold, ved en temperatur fra 5 °C til 10 °C.
5. Fremgangsmåden ifølge et hvilket som helst af kravene 1 til 4, hvor trin (c) udføres i et solvent valgt fra ethanol og acetone, eller fortrinsvis trin (c) udføres i acetone ved en temperatur fra 15 °C til 25 °C.
6. Fremgangsmåden ifølge et hvilket som helst af kravene 1 til 5, hvor trin (d) udføres ved at bringe D i kontakt med natriumhydroxid, i ethanol, og at reagere den opnåede blanding med jod, i ethanol, ved en temperatur fra 15 °C til 25 °C.
7. Fremgangsmåden ifølge et hvilket som helst af kravene 1 til 6, hvor trin (e) udføres ved omrøring af E i en refluksblanding af TFA og anisol i 5:1 volumenforhold.
8. Fremgangsmåden ifølge et hvilket som helst af kravene 1 til 7, hvor oprensning af det endelige produkt udføres ved rekrystallisering i vand.
9. Fremgangsmåden ifølge et hvilket som helst af kravene 1 til 8, hvor det endelige produkt opnås som en af dets hydratformer, fortrinsvis dets tri hydratform.
10. Fremgangsmåden ifølge et hvilket som helst af de foregående krav 1-9, hvor A fremstilles fra L-Homocystin med en fremgangsmåde omfattende trinnene: (a-1) at reagere L-Homocystin med benzylchloroformat for at give (2S,2S') 4,4'-disulfandiylbis(2-(benzyloxycarbonylamino)smørsyre) F; (b-1) at udføre en esterificeringsreaktion mellem F og ethanol for at give (2S,2S') diethyl 4,4'-disulfandiylbis(2-(benzyloxycarbonylamino)butanoat) G; (c-1) at oxidativt spalte disulfidbindingen af G for at give (S) ethyl 2-(benzyloxycarbonylamino) 4-(chlorsulfonyl)butanoat H og (d-1) at reagere H med neopentylalkohol for at give (S) ethyl 2-(benzyloxycarbonylamino) 4-(neopentyloxysulfonyl)butanoat A.
11. Fremgangsmåden ifølge krav 10, hvor trin (a-1) udføres i THF i tilstedeværelse af natriumhydroxid, ved en temperatur fra 15 °C til 25 °C.
12. Fremgangsmåden ifølge et hvilket som helst af kravene 10 og 11, hvor trin (b-1) udføres ved at reagere F med thionylchlorid, i ren ethanol, ved en temperatur fra 45 °C til 55 °C.
13. Fremgangsmåden ifølge et hvilket som helst af kravene 10 til 12, hvor trin (c-1) udføres ved at reagere G med chlor, i ethanol, ved en temperatur fra 5 til 10 °C.
14. Fremgangsmåden ifølge et hvilket som helst af kravene 10 til 13, hvor trin (d-1) udføres i tilstedeværelse af triethylamin, i toluen, ved en temperatur fra
15 °C til 25 °C.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10306099A EP2439192A1 (en) | 2010-10-07 | 2010-10-07 | Method for the preparation of (3S,3S') 4,4'-disulfanediylbis (3-aminobutane 1-sulfonic acid) |
| PCT/EP2011/067524 WO2012045849A1 (en) | 2010-10-07 | 2011-10-07 | Method for the preparation of (3s,3s') 4,4'-disulfanediylbis (3-aminobutane 1-sulfonic acid) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2625163T3 true DK2625163T3 (da) | 2018-10-15 |
Family
ID=43558332
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK18177972.9T DK3395796T3 (da) | 2010-10-07 | 2011-10-07 | Krystallinsk trihydratform af (3s,3s') 4,4'-disulfandiylbis (3-aminobutan-1-sulfonsyre) |
| DK11769843.1T DK2625163T3 (da) | 2010-10-07 | 2011-10-07 | Fremgangsmåde til fremstillingen af (3s,3s') 4,4'-disulfandiylbis (3-aminobutan 1- sulfonsyre) |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK18177972.9T DK3395796T3 (da) | 2010-10-07 | 2011-10-07 | Krystallinsk trihydratform af (3s,3s') 4,4'-disulfandiylbis (3-aminobutan-1-sulfonsyre) |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US9187418B2 (da) |
| EP (3) | EP2439192A1 (da) |
| JP (1) | JP5921556B2 (da) |
| KR (2) | KR101893894B1 (da) |
| CN (1) | CN103228624B (da) |
| AR (1) | AR083360A1 (da) |
| AU (1) | AU2011311483B2 (da) |
| BR (2) | BR112013008404B1 (da) |
| CA (2) | CA2813834C (da) |
| CY (2) | CY1120859T1 (da) |
| DK (2) | DK3395796T3 (da) |
| EA (1) | EA021612B1 (da) |
| ES (2) | ES2903434T3 (da) |
| HR (2) | HRP20220031T1 (da) |
| HU (2) | HUE040484T2 (da) |
| IL (1) | IL225557A (da) |
| LT (2) | LT3395796T (da) |
| MX (1) | MX2013003863A (da) |
| NZ (1) | NZ608971A (da) |
| PL (2) | PL2625163T3 (da) |
| PT (2) | PT3395796T (da) |
| RS (2) | RS57670B1 (da) |
| SI (2) | SI2625163T1 (da) |
| TW (1) | TWI532710B (da) |
| WO (1) | WO2012045849A1 (da) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2439192A1 (en) | 2010-10-07 | 2012-04-11 | Quantum Genomics | Method for the preparation of (3S,3S') 4,4'-disulfanediylbis (3-aminobutane 1-sulfonic acid) |
| EP2722327A1 (en) | 2012-10-22 | 2014-04-23 | Quantum Genomics | Crystalline phase of (3S,3S') 4,4'-disulfanediylbis (3-aminobutane 1-sulfonic acid) with L-lysine |
| US10501426B1 (en) | 2019-01-11 | 2019-12-10 | King Saud University | Synthesis of thiazole derivative as anticancer and anti-antibiotics resistant bacteria agent |
| TW202100146A (zh) | 2019-03-11 | 2021-01-01 | 法商量子基因科技有限公司 | 用於治療高血壓或心衰竭的化合物及包含其之組成物 |
| CN111892557B (zh) * | 2019-05-05 | 2022-11-08 | 河北圣泰材料股份有限公司 | 哌嗪类成膜离子液体的合成方法 |
| WO2022225712A1 (en) * | 2021-04-22 | 2022-10-27 | Teva Pharmaceuticals International Gmbh | Solid state forms of firibastat and processes for preparation thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5596095A (en) * | 1994-12-12 | 1997-01-21 | Procept, Inc. | Formation and utility of sulfonic acid protecting groups |
| ES2309336T3 (es) | 2002-07-16 | 2008-12-16 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Derivados de 4,4-ditiobis-(3-aminobutano-1-sulfanatos) nuevos y composiciones que los contienen. |
| FR2858617A1 (fr) * | 2003-08-06 | 2005-02-11 | Inst Nat Sante Rech Med | Derives de 4',4'-dithiobis-(3-aminobutane-1-sulfonate-1- sulfonates) nouveaux et compositions les contenant |
| CN101845003A (zh) * | 2010-01-29 | 2010-09-29 | 华东理工大学 | N-三(羟甲基)甲基-3-氨基丙磺酸化合物及其制备方法 |
| EP2439192A1 (en) | 2010-10-07 | 2012-04-11 | Quantum Genomics | Method for the preparation of (3S,3S') 4,4'-disulfanediylbis (3-aminobutane 1-sulfonic acid) |
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2010
- 2010-10-07 EP EP10306099A patent/EP2439192A1/en not_active Withdrawn
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2011
- 2011-10-06 TW TW100136334A patent/TWI532710B/zh active
- 2011-10-07 KR KR1020187008022A patent/KR101893894B1/ko active IP Right Grant
- 2011-10-07 SI SI201131578T patent/SI2625163T1/sl unknown
- 2011-10-07 PL PL11769843T patent/PL2625163T3/pl unknown
- 2011-10-07 RS RS20181090A patent/RS57670B1/sr unknown
- 2011-10-07 DK DK18177972.9T patent/DK3395796T3/da active
- 2011-10-07 HU HUE11769843A patent/HUE040484T2/hu unknown
- 2011-10-07 EA EA201300440A patent/EA021612B1/ru unknown
- 2011-10-07 HU HUE18177972A patent/HUE058031T2/hu unknown
- 2011-10-07 AU AU2011311483A patent/AU2011311483B2/en active Active
- 2011-10-07 JP JP2013532214A patent/JP5921556B2/ja active Active
- 2011-10-07 RS RS20211589A patent/RS62838B1/sr unknown
- 2011-10-07 KR KR1020137011888A patent/KR101869366B1/ko active IP Right Grant
- 2011-10-07 PL PL18177972T patent/PL3395796T3/pl unknown
- 2011-10-07 SI SI201132028T patent/SI3395796T1/sl unknown
- 2011-10-07 US US13/878,003 patent/US9187418B2/en active Active
- 2011-10-07 WO PCT/EP2011/067524 patent/WO2012045849A1/en active Application Filing
- 2011-10-07 LT LTEP18177972.9T patent/LT3395796T/lt unknown
- 2011-10-07 NZ NZ608971A patent/NZ608971A/en unknown
- 2011-10-07 BR BR112013008404-9A patent/BR112013008404B1/pt active IP Right Grant
- 2011-10-07 CA CA2813834A patent/CA2813834C/en active Active
- 2011-10-07 PT PT181779729T patent/PT3395796T/pt unknown
- 2011-10-07 EP EP18177972.9A patent/EP3395796B1/en active Active
- 2011-10-07 MX MX2013003863A patent/MX2013003863A/es active IP Right Grant
- 2011-10-07 PT PT11769843T patent/PT2625163T/pt unknown
- 2011-10-07 ES ES18177972T patent/ES2903434T3/es active Active
- 2011-10-07 EP EP11769843.1A patent/EP2625163B1/en active Active
- 2011-10-07 ES ES11769843.1T patent/ES2689246T3/es active Active
- 2011-10-07 HR HRP20220031TT patent/HRP20220031T1/hr unknown
- 2011-10-07 CA CA3016057A patent/CA3016057C/en active Active
- 2011-10-07 LT LTEP11769843.1T patent/LT2625163T/lt unknown
- 2011-10-07 DK DK11769843.1T patent/DK2625163T3/da active
- 2011-10-07 BR BR122021023430-2A patent/BR122021023430B1/pt active IP Right Grant
- 2011-10-07 CN CN201180056371.6A patent/CN103228624B/zh active Active
- 2011-10-11 AR ARP110103726A patent/AR083360A1/es active IP Right Grant
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- 2013-04-04 IL IL225557A patent/IL225557A/en active IP Right Grant
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- 2015-10-27 US US14/923,615 patent/US9340497B2/en active Active
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- 2018-09-19 CY CY181100970T patent/CY1120859T1/el unknown
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- 2022-01-13 CY CY20221100031T patent/CY1124919T1/el unknown
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