PL408028A1 - Bisphosphonic 2-(imidazo-1-yl)glutaric acid derivatives and method of their production - Google Patents
Bisphosphonic 2-(imidazo-1-yl)glutaric acid derivatives and method of their productionInfo
- Publication number
- PL408028A1 PL408028A1 PL408028A PL40802814A PL408028A1 PL 408028 A1 PL408028 A1 PL 408028A1 PL 408028 A PL408028 A PL 408028A PL 40802814 A PL40802814 A PL 40802814A PL 408028 A1 PL408028 A1 PL 408028A1
- Authority
- PL
- Poland
- Prior art keywords
- imidazo
- bisphosphonic
- glutaric acid
- acid
- acid derivatives
- Prior art date
Links
- 150000002310 glutaric acid derivatives Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 abstract 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 abstract 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 235000013922 glutamic acid Nutrition 0.000 abstract 1
- 239000004220 glutamic acid Substances 0.000 abstract 1
- 229940015043 glyoxal Drugs 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 229910017053 inorganic salt Inorganic materials 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 229920002866 paraformaldehyde Polymers 0.000 abstract 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Abstract
Wynalazek dotyczy bisfosfonowych pochodnych kwasu 2-(imidazo-1-yl)glutarowego przedstawionych wzorem ogólnym 1, w którym R1 oznacza pierścień imidazolu podstawiony w pozycji 1 a R2 atom wodoru lub R1 oznacza atom wodoru a R2 pierścień imidazolu podstawiony w pozycji 1. Wynalazek ujawnia (również sposób wytwarzania bisfosfonowych pochodnych kwasu 2-(imidazo-1-yl)glutarowego przedstawionych wzorem 1, który polega na tym, że jedną część molową kwasu glutaminowego, poddaje się reakcji z co najmniej jedną częścią glioksalu, co najmniej jedną częścią amoniaku, co najmniej jedną częścią formaldehydu wybranego z grupy obejmującej formalinę, trioksan lub paraform oraz co najmniej dwiema częściami zasady w temperaturze 273-373 K, po czym z mieszaniny odparowuje się lotne składniki pod zmniejszonym ciśnieniem w temperaturze 293-373 K, a otrzymaną pozostałość neutralizuje się wodnym roztworem kwasu nieorganicznego, oddziela się powstałą sól nieorganiczną i odparowuje do sucha pod zmniejszonym ciśnieniem w temperaturze 293-373 K i tak otrzymaną pozostałość rozpuszcza się w wodzie, poddaje się reakcji z trójchlorkiem fosforu, następnie hydrolizuje i w wyniku oczyszczania na żywicy jonowymiennej wydziela się odpowiednie bisfosfonowe pochodne kwasu 2-(imidazo-1-yl)glutarowego.The invention relates to bisphosphonic derivatives of 2- (imidazo-1-yl) glutaric acid represented by the general formula 1, wherein R1 is an imidazole ring substituted in position 1 and R2 is a hydrogen atom or R1 is a hydrogen atom and R2 ring imidazole is substituted in position 1. The invention discloses (also a method for producing bisphosphonic 2- (imidazo-1-yl) glutaric acid derivatives represented by formula 1, which consists in that one molar part of glutamic acid is reacted with at least one part of glyoxal, at least one part of ammonia, which at least one part of formaldehyde selected from the group consisting of formalin, trioxane or paraform and at least two parts of base at 273-373 K, after which the volatile components are evaporated under reduced pressure at 293-373 K, and the residue obtained is neutralized with aqueous inorganic acid solution, the resulting inorganic salt is separated and evaporated to dryness under reduced pressure at a temperature of 293-373 K, and the residue thus obtained is dissolved in water, reacted with phosphorus trichloride, then hydrolyzed and the corresponding bisphosphonic acid 2- (imidazo-1 acid derivatives are isolated on the ion exchange resin purification) yl) glutaric acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL408028A PL408028A1 (en) | 2014-04-28 | 2014-04-28 | Bisphosphonic 2-(imidazo-1-yl)glutaric acid derivatives and method of their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL408028A PL408028A1 (en) | 2014-04-28 | 2014-04-28 | Bisphosphonic 2-(imidazo-1-yl)glutaric acid derivatives and method of their production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL408028A1 true PL408028A1 (en) | 2015-02-16 |
Family
ID=52464736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL408028A PL408028A1 (en) | 2014-04-28 | 2014-04-28 | Bisphosphonic 2-(imidazo-1-yl)glutaric acid derivatives and method of their production |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL408028A1 (en) |
-
2014
- 2014-04-28 PL PL408028A patent/PL408028A1/en unknown
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