DK147261B - Analogifremgangsmaade til fremstilling af mono(2-ammonium-2-hydroxymethyl-1,3-propandiol)(2r-cis)-(3-methyloxiranyl)phosphonat - Google Patents
Analogifremgangsmaade til fremstilling af mono(2-ammonium-2-hydroxymethyl-1,3-propandiol)(2r-cis)-(3-methyloxiranyl)phosphonat Download PDFInfo
- Publication number
- DK147261B DK147261B DK442080AA DK442080A DK147261B DK 147261 B DK147261 B DK 147261B DK 442080A A DK442080A A DK 442080AA DK 442080 A DK442080 A DK 442080A DK 147261 B DK147261 B DK 147261B
- Authority
- DK
- Denmark
- Prior art keywords
- methyloxiranyl
- cis
- ammonium
- hydroxymethyl
- phosphonate
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract description 3
- DYASJGUMFFSTDH-STHAYSLISA-N C[C@@H]1O[C@@H]1OP(O)=O Chemical compound C[C@@H]1O[C@@H]1OP(O)=O DYASJGUMFFSTDH-STHAYSLISA-N 0.000 title description 9
- 238000002360 preparation method Methods 0.000 title description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 abstract description 5
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- YMDXZJFXQJVXBF-STHAYSLISA-N fosfomycin Chemical compound C[C@@H]1O[C@@H]1P(O)(O)=O YMDXZJFXQJVXBF-STHAYSLISA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 4
- -1 3-methyloxiranyl Chemical group 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 229940035437 1,3-propanediol Drugs 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65502—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a three-membered ring
- C07F9/65505—Phosphonic acids containing oxirane groups; esters thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Cosmetics (AREA)
Description
i 147261
Opfindelsen angår en analogifremgangsmåde til fremstilling af et hidtil ukendt opløseligt salt af (2R-cis)-(3-methyloxiranyl)phosphonsyre.
Det omhandlede salt er mono(2-ammonium-2-hydroxymethyl-5 1,3-propandiol)(2R~cis)-(3-methyloxiranyl)phosphonatet med formlen 0 Q> ? H°-fH2 HO-CH -C-NH · HO^ \-/ 21 /\7\ H°-CH2 Η' ^ Ή (2R-cis)-(3-methyloxiranyl)phosphonsyre er også kendt som fosfomycin (Merck Index, 9. udgave, 4110).
Fosfomycin og salte heraf med ikke-toksiske baser anvendes 10 i vid udstrækning inden for den humane og veterinære medicin til at hæmme væksten af gram-positive og gram-negative pathogene bakterier.
Dansk patentansøgning nr. 3023/79 omhandler bis(2-ammonium-2-hydroxymethyl-l,3-propandiol)(2R-cis)-(3-methyloxiranyl)phosphonatet, der udviser en tolerance og bio-tilgængelighed, der er betydelig bedre end natrium- og calciumsaltene af fosfomycin.
Imidlertid giver bis(2-ammonium-2-hydroxymethyl-l,3-propandiol ) ( 2R- c i s) - (3-methyloxiranyl) pho sphonat en særdeles viskøs opløsning, hvilket gør det vanskeligt at administrere ved injektion.
Det har nu vist sig, at det omhandlede mono(2-ammonium-2-hydroxymethyl-1,3-propandiol)(2R-cis)-(3-methyloxiranyl)-phosphonat samtidig med at det bibeholder fordelene ved bis(2-ammonium-2-hydroxymethyl-l,3-propandiol)(2R-cis)- 2 147261 ‘ · (3-methyloxiranyl)phosphonat har den fordel, at det giver opløsninger, der er mindre viskøse end de, der fås, når man anvender bis(2-ammonium-2-hydroxy-methyl-1,3-propandiol)(2R-cis)-(3-methyloxiranyl)-5 phosphonat svarende til samme mængde fosfomycin.
Mere specielt udviser en opløsning bestående af henholdsvis 688 mg og 1377 mg af bis(2-ammonium-2-hydroxymethyl- 1,3-propandiol)(2R-cis)-(3-methyloxiranyl)phosphonat (svarende til henholdsvis 250 og 500 mg fosfomycin) 10 i 2,5 ml vand en viskositet på henholdsvis 4,8 og 7,2 cP ved 25 °C. De tilsvarende opløsninger udviser ved opløsning af henholdsvis 470 mg og 940 mg mono-(2-ammonium-2-hydroxymethyl-l,3-propandiol)(2R-cis)-(3-methyloxiranyl)phosphonat i 2,5 ml vand ved 25 °C 15 en viskositet på henholdsvis 3,9 og 5,0 cP.
Det omhandlede mono(2-ammonium-2-hydroxymethyl-l,3-propandiol)(2R-cis)-(3-methyloxiranyl)phosphonat fremstilles ifølge opfindelsen ved at bis {-2-ammonium-2-hydroxymethyl-l,3-propandiol)(2R-cis)-(3-methyl-20 oxiranyl)phosphonat fremstillet som beskrevet i dansk patentansøgning nr. 3023/79 omsættes med en alkan-, aren- eller aralkansulfonsyre. Fremstillingen af det omhandlede- salt' og de fysisk-kemiske data for den fremstillede forbindelse, er angivet i det følgende eksempel.
Eksempel
En opløsning forud opvarmet ved 75° C bestående af 262,5 g (1,58 mol) monohydratiseret 4-toluensulfonsyre i 1300 ml absolut ethanol sættes til en suspension af 500 mg (1,315 mol) bis(2-ammonium-2-hydroxymethyl-l,3-propandiol)(2R-cis)-(3-methyloxiranyl)phosphonat i 300 ml absolut ethanol, og der opvarmes under omrøring ved 70 - 75° C.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT26581/79A IT1124610B (it) | 1979-10-18 | 1979-10-18 | Mono(2-ammonio-2-idrossimetil-1,3-propandiolo) (2r-cis)-(o-metilossiranil)fosfonato |
| IT2658179 | 1979-10-18 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK442080A DK442080A (da) | 1981-04-19 |
| DK147261B true DK147261B (da) | 1984-05-28 |
| DK147261C DK147261C (da) | 1984-11-26 |
Family
ID=11219823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK442080A DK147261C (da) | 1979-10-18 | 1980-10-17 | Analogifremgangsmaade til fremstilling af mono(2-ammonium-2-hydroxymethyl-1,3-propandiol)(2r-cis)-(3-methyloxiranyl)phosphonat |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4863908A (da) |
| EP (1) | EP0027597B1 (da) |
| JP (1) | JPS5677290A (da) |
| AT (1) | ATE2005T1 (da) |
| AU (1) | AU532089B2 (da) |
| BE (1) | BE885756A (da) |
| BG (1) | BG61368B2 (da) |
| CA (1) | CA1163274A (da) |
| CH (1) | CH644613A5 (da) |
| DE (1) | DE3061359D1 (da) |
| DK (1) | DK147261C (da) |
| ES (1) | ES495870A0 (da) |
| FR (1) | FR2467856A1 (da) |
| GB (1) | GB2062640B (da) |
| GR (1) | GR70312B (da) |
| IE (1) | IE50319B1 (da) |
| IL (1) | IL61221A (da) |
| IT (1) | IT1124610B (da) |
| LU (1) | LU88335I2 (da) |
| MX (1) | MX9203181A (da) |
| NL (1) | NL930041I2 (da) |
| YU (1) | YU41742B (da) |
| ZA (1) | ZA806308B (da) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1136652B (it) * | 1981-06-04 | 1986-09-03 | Crinos Industria Farmaco | Compesizione farmaceutica di fosfomicina in compresse da succhiare |
| CH660305A5 (de) * | 1984-10-05 | 1987-04-15 | Schering Spa | Wasserloesliche pharmazeutische zusammensetzungen auf der basis von salzen der (-)cis-1,2-epoxypropylphosphonsaeure mit aminosaeuren. |
| US5191094A (en) * | 1989-07-27 | 1993-03-02 | Zambon Group S.P.A. | Mono (2-ammonium-2-hydroxymethyl-1,3-propanediol) (2R,cis)-1,2-epoxypropyl-phosphonate with improved characteristics of stability and processing |
| IT1231013B (it) * | 1989-07-27 | 1991-11-08 | Zambon Spa | Mono (2 ammonio 2 idrossimetil 1,3 propandiolo)(2r,cis) 1,2 epossipropil fosfonato avente migliorate caratteristiche di stabilita' e lavorabilita'. |
| ITMI20021725A1 (it) | 2002-08-01 | 2002-10-31 | Zambon Spa | Composizioni farmaceutiche ad attivita' antibiotica. |
| ES2244333B1 (es) * | 2004-05-18 | 2006-08-01 | Simbec Iberica, Sl | Preparado farmaceutico oral de fosfomicina estable y apto para diabeticos. |
| EP1762573A1 (en) | 2005-09-08 | 2007-03-14 | Interquim, S.A. De C.V. | A process for the preparation of fosfomycin salts |
| ES2345591B1 (es) * | 2009-03-10 | 2011-07-21 | Labiana Pharmaceuticals, S.L. | Procedimiento para la preparacion de fosfomicina trometamol. |
| CN102351902A (zh) * | 2011-08-12 | 2012-02-15 | 山西仟源制药股份有限公司 | 磷霉素单氨丁三醇的制备方法 |
| CN102807586B (zh) | 2012-08-31 | 2015-05-13 | 东北制药集团股份有限公司 | 磷霉素氨盐的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3322767A (en) * | 1963-06-03 | 1967-05-30 | Gabriel G Nabas | Tham salts |
| US3639590A (en) * | 1967-07-25 | 1972-02-01 | Merck & Co Inc | Antibacterial composition containing (-) (cis-1 2-epoxypropyl) phosphoric acid |
| US3641063A (en) * | 1968-01-22 | 1972-02-08 | Merck & Co Inc | Antibiotic purification process |
| US3914231A (en) * | 1970-09-04 | 1975-10-21 | Merck & Co Inc | ({31 )(Cis-1,2-epoxypropyl)-phosphonic acid and salts thereof |
| US3940483A (en) * | 1971-02-05 | 1976-02-24 | E. R. Squibb & Sons, Inc. | Antibiotic compositions and method |
| DE2134672A1 (de) * | 1971-07-08 | 1973-01-25 | Josef Dipl Chem Dr Rer N Klosa | Wasserloesliches acetylsalicylsaeuresalz, dessen herstellung, zubereitung und anwendung |
| IT1112282B (it) * | 1978-07-19 | 1986-01-13 | Zambon Spa | Bis-(2-ammonio-2-idrossimetil-1,3-propandiolo)(2r-cis)-(3-metilossiranil)fosfonato |
| GB2158828B (en) * | 1984-04-25 | 1987-12-09 | Espanola De La Penicilina Y An | Salts of fosfomycin |
-
1979
- 1979-10-18 IT IT26581/79A patent/IT1124610B/it active
-
1980
- 1980-10-03 IE IE2062/80A patent/IE50319B1/en not_active IP Right Cessation
- 1980-10-07 IL IL61221A patent/IL61221A/xx not_active IP Right Cessation
- 1980-10-08 AT AT80106108T patent/ATE2005T1/de active
- 1980-10-08 EP EP80106108A patent/EP0027597B1/en not_active Expired
- 1980-10-08 DE DE8080106108T patent/DE3061359D1/de not_active Expired
- 1980-10-10 GB GB8032736A patent/GB2062640B/en not_active Expired
- 1980-10-13 ES ES495870A patent/ES495870A0/es active Granted
- 1980-10-13 CH CH762280A patent/CH644613A5/it not_active IP Right Cessation
- 1980-10-14 ZA ZA00806308A patent/ZA806308B/xx unknown
- 1980-10-15 GR GR63159A patent/GR70312B/el unknown
- 1980-10-16 CA CA000362531A patent/CA1163274A/en not_active Expired
- 1980-10-16 AU AU63418/80A patent/AU532089B2/en not_active Expired
- 1980-10-16 BE BE0/202498A patent/BE885756A/fr not_active IP Right Cessation
- 1980-10-17 YU YU2668/80A patent/YU41742B/xx unknown
- 1980-10-17 FR FR8022221A patent/FR2467856A1/fr active Granted
- 1980-10-17 DK DK442080A patent/DK147261C/da not_active IP Right Cessation
- 1980-10-17 JP JP14455280A patent/JPS5677290A/ja active Granted
-
1987
- 1987-09-15 US US07/097,425 patent/US4863908A/en not_active Expired - Lifetime
-
1992
- 1992-06-23 MX MX9203181A patent/MX9203181A/es unknown
-
1993
- 1993-05-28 NL NL930041C patent/NL930041I2/nl unknown
- 1993-06-24 LU LU88335C patent/LU88335I2/fr unknown
-
1994
- 1994-02-25 BG BG98592A patent/BG61368B2/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES8200700A1 (es) | 1981-11-16 |
| EP0027597B1 (en) | 1982-12-15 |
| EP0027597A1 (en) | 1981-04-29 |
| IE50319B1 (en) | 1986-04-02 |
| DE3061359D1 (en) | 1983-01-20 |
| ATE2005T1 (de) | 1982-12-15 |
| BG61368B2 (bg) | 1997-06-30 |
| US4863908A (en) | 1989-09-05 |
| DK147261C (da) | 1984-11-26 |
| IT1124610B (it) | 1986-05-07 |
| JPS6317836B2 (da) | 1988-04-15 |
| FR2467856B1 (da) | 1984-10-05 |
| CH644613A5 (it) | 1984-08-15 |
| MX9203181A (es) | 1992-07-01 |
| ZA806308B (en) | 1981-08-26 |
| IT7926581A0 (it) | 1979-10-18 |
| DK442080A (da) | 1981-04-19 |
| JPS5677290A (en) | 1981-06-25 |
| NL930041I2 (nl) | 1993-11-16 |
| YU41742B (en) | 1987-12-31 |
| YU266880A (en) | 1983-06-30 |
| AU6341880A (en) | 1981-04-30 |
| BE885756A (fr) | 1981-04-16 |
| GB2062640B (en) | 1983-09-14 |
| IL61221A (en) | 1985-02-28 |
| NL930041I1 (nl) | 1993-08-02 |
| AU532089B2 (en) | 1983-09-15 |
| GR70312B (da) | 1982-09-09 |
| CA1163274A (en) | 1984-03-06 |
| IL61221A0 (en) | 1980-12-31 |
| FR2467856A1 (fr) | 1981-04-30 |
| ES495870A0 (es) | 1981-11-16 |
| IE802062L (en) | 1981-04-18 |
| LU88335I2 (fr) | 1994-05-04 |
| GB2062640A (en) | 1981-05-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUP | Patent expired |