PL408026A1 - 6-amino-2-(imidazo-1-yl)-1-hydroxy hexylideno bisphosphonic acid and 2-amino-6-(imidazo-1-yl)-1-hydroxy hexylideno bisphosphonic acid and method of their production - Google Patents
6-amino-2-(imidazo-1-yl)-1-hydroxy hexylideno bisphosphonic acid and 2-amino-6-(imidazo-1-yl)-1-hydroxy hexylideno bisphosphonic acid and method of their productionInfo
- Publication number
- PL408026A1 PL408026A1 PL408026A PL40802614A PL408026A1 PL 408026 A1 PL408026 A1 PL 408026A1 PL 408026 A PL408026 A PL 408026A PL 40802614 A PL40802614 A PL 40802614A PL 408026 A1 PL408026 A1 PL 408026A1
- Authority
- PL
- Poland
- Prior art keywords
- acid
- imidazo
- amino
- formula
- temperature
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 abstract 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 229940015043 glyoxal Drugs 0.000 abstract 1
- 229910017053 inorganic salt Inorganic materials 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229920002866 paraformaldehyde Polymers 0.000 abstract 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Abstract
Przedmiotem wynalazku jest kwas 6-amino-2-(imidazo-1-yl)-1-hydroksyheksylidenobisfosfonowy o wzorze 1 oraz kwas 2-amino-6-(imidazo-1-yl)-1-hydroksyheksylidenobisfosfonowy o wzorze 2. Przedmiotem wynalazku jest również sposób wytwarzania kwasu przedstawionego wzorem 1 oraz kwasu przedstawionego wzorem 2, polegający na tym, że odpowiedni kwas 6-(alkiloksykarbonyloamino)-2-aminoheksanowy przedstawiony wzorem 3, w którym R oznacza grupę benzyloksykarbonylową lub tertbutoksykarbonylową lub kwas 2-(alkiloksykarbonyloamino)-6-aminoheksanowy przedstawiony wzorem 4, w którym R ma znaczenie jak podane poprzednio, poddaje się reakcji z co najmniej jedną częścią glioksalu, co najmniej jedną częścią amoniaku, co najmniej jedną częścią formaldehydu w substancji wybranej z grupy obejmującej formalinę, trioksan lub paraform oraz z co najmniej jedną częścią zasady, przy czym reakcję prowadzi się w temperaturze 298-373 K w roztworze wodnym, aż do przereagowania substratów, po czym z mieszaniny usuwa się wszystkie lotne składniki przez destylację pod zmniejszonym ciśnieniem, a pozostałość poddaje się w drugim etapie hydrolizie wodnym roztworem kwasu nieorganicznego, w temperaturze 273-373 K i odparowuje do sucha pod zmniejszonym ciśnieniem w temperaturze 293-373 K, i tak otrzymaną pozostałość traktuje się metanolem, oddziela się powstałą sól nieorganiczną i ponownie odparowuje się do sucha pod zmniejszonym ciśnieniem w temperaturze 293-373 K, przy czym w kolejnym etapie, otrzymaną pozostałość rozpuszcza się w wodzie, poddaje się reakcji z trójchlorkiem fosforu, następnie hydrolizuje i wydziela się odpowiednio kwas 6-amino-2-(imidazo-1-yl)-1-hydroksyheksylidenobisfosfonowy i kwas 2-amino-6-(imidazo-1-yl)-1-hydroksyheksylidenobisfosfonowy.The subject of the invention is 6-amino-2-(imidazo-1-yl)-1-hydroxyhexylidenebisphosphonic acid of formula 1 and 2-amino-6-(imidazo-1-yl)-1-hydroxyhexylidenebisphosphonic acid of formula 2. The subject of the invention is also a method for preparing the acid represented by formula 1 and the acid represented by formula 2, consisting in the corresponding 6-(alkyloxycarbonylamino)-2-aminohexanoic acid represented by formula 3, where R is a benzyloxycarbonyl or tert-butoxycarbonyl group or 2-(alkyloxycarbonylamino)-6 acid -aminohexane represented by formula 4, where R is as previously given, is reacted with at least one part of glyoxal, at least one part of ammonia, at least one part of formaldehyde in a substance selected from the group consisting of formalin, trioxane or paraform and with at least at least one part of the base, the reaction is carried out at a temperature of 298-373 K in an aqueous solution until the reactants are reacted, then all volatile components are removed from the mixture by distillation under reduced pressure, and the residue is hydrolyzed with an aqueous solution in the second stage inorganic acid, at a temperature of 273-373 K and evaporated to dryness under reduced pressure at a temperature of 293-373 K, and the residue thus obtained is treated with methanol, the inorganic salt formed is separated and evaporated to dryness again under reduced pressure at a temperature of 293-373 K, and in the next step, the obtained residue is dissolved in water, reacted with phosphorus trichloride, then hydrolyzed and 6-amino-2-(imidazo-1-yl)-1-hydroxyhexylidenebisphosphonic acid and 2- amino-6-(imidazo-1-yl)-1-hydroxyhexylidenebisphosphonic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL408026A PL408026A1 (en) | 2014-04-28 | 2014-04-28 | 6-amino-2-(imidazo-1-yl)-1-hydroxy hexylideno bisphosphonic acid and 2-amino-6-(imidazo-1-yl)-1-hydroxy hexylideno bisphosphonic acid and method of their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL408026A PL408026A1 (en) | 2014-04-28 | 2014-04-28 | 6-amino-2-(imidazo-1-yl)-1-hydroxy hexylideno bisphosphonic acid and 2-amino-6-(imidazo-1-yl)-1-hydroxy hexylideno bisphosphonic acid and method of their production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL408026A1 true PL408026A1 (en) | 2015-02-16 |
Family
ID=52464734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL408026A PL408026A1 (en) | 2014-04-28 | 2014-04-28 | 6-amino-2-(imidazo-1-yl)-1-hydroxy hexylideno bisphosphonic acid and 2-amino-6-(imidazo-1-yl)-1-hydroxy hexylideno bisphosphonic acid and method of their production |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL408026A1 (en) |
-
2014
- 2014-04-28 PL PL408026A patent/PL408026A1/en unknown
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