SE444942B - Forfarande for framstellning av s-trietylfosfinguld-2,3,4,6-tetra-o-acetyl-1-tio-beta-d-glukopyranosid (auranofin) - Google Patents
Forfarande for framstellning av s-trietylfosfinguld-2,3,4,6-tetra-o-acetyl-1-tio-beta-d-glukopyranosid (auranofin)Info
- Publication number
- SE444942B SE444942B SE7806639A SE7806639A SE444942B SE 444942 B SE444942 B SE 444942B SE 7806639 A SE7806639 A SE 7806639A SE 7806639 A SE7806639 A SE 7806639A SE 444942 B SE444942 B SE 444942B
- Authority
- SE
- Sweden
- Prior art keywords
- acetyl
- tetra
- auranofin
- glucopyranoside
- gold
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 6
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 title claims abstract description 5
- AUJRCFUBUPVWSZ-XTZHGVARSA-M auranofin Chemical compound CCP(CC)(CC)=[Au]S[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O AUJRCFUBUPVWSZ-XTZHGVARSA-M 0.000 title abstract description 4
- 229960005207 auranofin Drugs 0.000 title abstract description 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims abstract 2
- 239000002904 solvent Substances 0.000 claims description 4
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 229960002246 beta-d-glucopyranose Drugs 0.000 claims 1
- 230000002456 anti-arthritic effect Effects 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XHVAWZZCDCWGBK-WYRLRVFGSA-M Aurothioglucose Chemical compound OC[C@H]1O[C@H](S[Au])[C@H](O)[C@@H](O)[C@@H]1O XHVAWZZCDCWGBK-WYRLRVFGSA-M 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- IRPYFWIZKIOHQN-XTZHGVARSA-N gold;[(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-sulfanyloxan-2-yl]methyl acetate;triethylphosphane Chemical compound [Au].CC[PH+](CC)CC.CC(=O)OC[C@H]1O[C@@H]([S-])[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O IRPYFWIZKIOHQN-XTZHGVARSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- XYYVDQWGDNRQDA-UHFFFAOYSA-K trichlorogold;trihydrate;hydrochloride Chemical compound O.O.O.Cl.Cl[Au](Cl)Cl XYYVDQWGDNRQDA-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon, or a metal, e.g. chelates, vitamin B12
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/12—Gold compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
Description
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7806659-5.
utmärkt utbyte och renhet.. , _
Reaktionen enligt uppfinningen utförs genom att man låter den nya
föreningen S-guld-2,3,l+,6-tetra-O-acetyl-l-tio-B-D-glukopyranos reagera med en
stökiometrisk mängd av trietylfosfin i ett inert aprotiskt halogenerat kolväte-
lösningsmedel, i vilket de båda reaktanterna är lösliga såsom kloroform,
koltetraklorid, etylentetraklorid eller metylenklorid. Metylenklorid är ett mycket
lämpligt lösningsmedel.
_ Reaktionen körs lämpligen och fortgår till fullbordan vid rumstemperatur
nästan genast". Den önskade auranofinprodukten isoleras lätt och renas genom
a kända metoder inom tekniken.
Det nya. guldsaltetü) kan även framställas genom andra förfaranden,
vilket torde ínses avfackmannen på området, t.ex.' genom Q-acetylering av
aurotioglukos (Solganol), men de förfaranden som beskrivs i detalj i det följande
är enkla och ger utmärkta utbyten av ren produkt.
Det .följande exemplet är avsett att belysa. men inte begränsa uppfin-
ningen. Andra modifikationer är uppenbara för fackmannen. 'Alla temperaturer
är i celsiusgrader. i i
Exemæl i
Tiodiglykol, 6,41 g (0,052 mol), i etanol (20 ml) sattes till. 10 g (0,025 mol)
guldsyraklorídtrihydrat i vatten (50 ml) vid 0°C. Till 'detta sattes, efter
filtrering, en lösning av 9,4 g (0,026 mol) 2,3,l4,6-tetra-O-acetyl-l-tio-B-D-
glukopyranos och 6,6g (0,0l:8 mol) kaliumkarbonat i 25 ml etanol och 60 ml
vattemEfter omrörning l timme vid 0° (skumning) avlägsnades fällningen genom
filtrering, tvättades med vatten och lufttorkades. Omkristallísation ur isopropa- '
nol-eter gav S-guId-Z,3,4,6-tetra-0-acetyl-l-tio-B-D-glukopyranos som en ljusgul
.fast substans, smältpunkt 1l46-ll+8°; [qlâs = -56,9 (196 metanol). Trietylfosfin
l0,2g (1,7 mmol, 0,25 ml) sattes till 1,03 (1,7 mmol) S-guld-2,3,4,6-tetra-O-
acetyl-l-tio-B-D-glukopyranos i 6 ml kloroform som höllsnvid rumstemperatur.
Lösningen blev genast färglös och efter 15 minuter avlägsnades lösningsmedlet
'vid minskat tryck. Kromatografi (silikagel/etylacetat) gav 0,76 g auranofin som
en vit fast substans, som omkristalliserades ur metanol .(3 ml), vilket gav 0,55 g
»(45%) produkt, smänpunk: 1064029; (u )25= -ss,1 (196 rnefanoi).
Claims (1)
- 7806639-6 3 t PATENTKRAV l. Sätt att framställa auranofln med formeln :där Ac är acetyl, k ä n n e t 'e c kn a t av att man låter S-guld-Z,3,4,6-tetra-O-acetyl4l-tio-ß-D- glukopyranos reagera med trietylfosfin i ett halogenerat kolväteiösningsmedel vid ungefär rumstemperatur.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7806639A SE444942B (sv) | 1978-06-07 | 1978-06-07 | Forfarande for framstellning av s-trietylfosfinguld-2,3,4,6-tetra-o-acetyl-1-tio-beta-d-glukopyranosid (auranofin) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7806639A SE444942B (sv) | 1978-06-07 | 1978-06-07 | Forfarande for framstellning av s-trietylfosfinguld-2,3,4,6-tetra-o-acetyl-1-tio-beta-d-glukopyranosid (auranofin) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7806639L SE7806639L (sv) | 1978-12-11 |
| SE444942B true SE444942B (sv) | 1986-05-20 |
Family
ID=20335147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7806639A SE444942B (sv) | 1978-06-07 | 1978-06-07 | Forfarande for framstellning av s-trietylfosfinguld-2,3,4,6-tetra-o-acetyl-1-tio-beta-d-glukopyranosid (auranofin) |
Country Status (1)
| Country | Link |
|---|---|
| SE (1) | SE444942B (sv) |
-
1978
- 1978-06-07 SE SE7806639A patent/SE444942B/sv not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE7806639L (sv) | 1978-12-11 |
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| NUG | Patent has lapsed |
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