JP2008525432A - 〔1−ヒドロキシ−2−(3−ピリジニル)エチリデン〕ビスホスホン酸及びその半−5水和物モノナトリウム塩の製造方法 - Google Patents
〔1−ヒドロキシ−2−(3−ピリジニル)エチリデン〕ビスホスホン酸及びその半−5水和物モノナトリウム塩の製造方法 Download PDFInfo
- Publication number
- JP2008525432A JP2008525432A JP2007548122A JP2007548122A JP2008525432A JP 2008525432 A JP2008525432 A JP 2008525432A JP 2007548122 A JP2007548122 A JP 2007548122A JP 2007548122 A JP2007548122 A JP 2007548122A JP 2008525432 A JP2008525432 A JP 2008525432A
- Authority
- JP
- Japan
- Prior art keywords
- pyridinyl
- ethylidene
- hydroxy
- acid
- bisphosphonic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- IIDJRNMFWXDHID-UHFFFAOYSA-N Risedronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CC1=CC=CN=C1 IIDJRNMFWXDHID-UHFFFAOYSA-N 0.000 title claims abstract description 28
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- XVCCOEWNFXXUEV-UHFFFAOYSA-N 2-pyridin-3-ylacetic acid;hydrochloride Chemical compound Cl.OC(=O)CC1=CC=CN=C1 XVCCOEWNFXXUEV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000001035 drying Methods 0.000 claims abstract description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 6
- PCTGJJZEWJRHFL-UHFFFAOYSA-N pyridin-3-yl acetate;hydrochloride Chemical compound Cl.CC(=O)OC1=CC=CN=C1 PCTGJJZEWJRHFL-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 235000017550 sodium carbonate Nutrition 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- WGNUNYPERJMVRM-UHFFFAOYSA-M 2-pyridin-3-ylacetate Chemical compound [O-]C(=O)CC1=CC=CN=C1 WGNUNYPERJMVRM-UHFFFAOYSA-M 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 3
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- FGBXDQWECLPOGZ-UHFFFAOYSA-N [Na].O.O.O.O.O.[Na] Chemical compound [Na].O.O.O.O.O.[Na] FGBXDQWECLPOGZ-UHFFFAOYSA-N 0.000 abstract 2
- 238000001914 filtration Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 229960000759 risedronic acid Drugs 0.000 description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 5
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WGNUNYPERJMVRM-UHFFFAOYSA-N 3-pyridylacetic acid Chemical compound OC(=O)CC1=CC=CN=C1 WGNUNYPERJMVRM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 208000001132 Osteoporosis Diseases 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 229940122361 Bisphosphonate Drugs 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 208000008924 Femoral Fractures Diseases 0.000 description 1
- 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
- 208000010191 Osteitis Deformans Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000027868 Paget disease Diseases 0.000 description 1
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000004663 bisphosphonates Chemical class 0.000 description 1
- 230000003913 calcium metabolism Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 208000027202 mammary Paget disease Diseases 0.000 description 1
- 150000004686 pentahydrates Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229940089617 risedronate Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 238000010671 solid-state reaction Methods 0.000 description 1
- 206010041569 spinal fracture Diseases 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
-
- 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Seasonings (AREA)
Abstract
【解決手段】3−ピリジニル酢酸塩酸塩の水溶液を0〜5℃で3塩化リンに滴加して反応させ、過剰の3塩化リンを除去し、水を加えて反応生成物を加水分解し、水に懸濁している結晶質〔1−ヒドロキシ−2−(3−ピリジニル)エチリデン〕ビスホスホン酸を単離し、ソーダ灰を加えそして得られた混合物を乾燥して〔1−ヒドロキシ−2−(3−ピリジニル)エチリデン〕ビスホスホン酸の半−5水和物モノナトリウム塩を得る。
Description
式(1)
〔1−ヒドロキシ−2−(3−ピリジニル)エチリデン〕ビスホスホン酸の製造方法は、主に3−ピリジニル酢酸と亜リン酸とリン酸塩化物との反応によるものである。
特許文献1には、3−ピリジニル酢酸を3塩化リンを添加して、亜リン酸と反応させる方法が開示されている。
意外にも、本発明者らは、〔1−ヒドロキシ−2−(3−ピリジニル)エチリデン〕ビスホスホン酸及びその半5−水和物モノナトリウム塩の製造方法において3塩化リンを溶媒兼反応試薬として用いると、反応が均一系で行われることを見出した。また、もし正しいpHと乾燥条件を守れば、リセドロン酸の収率が82%、その半−5水和物モノナトリウムの収率が67%は達成できる。リセドロン酸の結晶化が反応中に生ずるリン酸、亜リン酸及び塩酸の除去を促進する。
適切な温度で乾燥することで最終生成物は
式(2):
次に実施例によって本発明を例証するが、これらは本発明を制限するものではない。
35.75g(0.206モル)の3−ピリジニル酢酸塩酸塩の水溶液を0〜5℃の温度に冷却した169.93g(1.23モル)の3塩化リン酸中に、0〜5℃の温度で激しい混合下に1時間かけて滴加した。次いで反応混合物を75〜80℃の温度に徐々に加熱し、そして固体状態の反応混合物が得られる迄この温度を維持した。反応に用いた過剰の3塩化リンを減圧下に留去した。次いで、200mlの水を加え、混合物を6時間沸騰させて加水分解した。冷却後、混合物を濾過し、水洗し、乾燥した。結果として、48g(収率82%)の〔1−ヒドロキシ−2−(3−ピリジニル)エチリデン〕ビスホスホン酸を得た。
13PNMR(D2O)δ=18.2
20gの1−〔ヒドロキシ−2−(3−ピリジニル)エチリデン〕ビスホスホン酸を100mlの水に懸濁させ、そして100〜102℃の温度と加熱してから6.58gの45%ソーダ灰をpHが4.9〜5.0になる迄滴加した。この反応混合物を約2時間沸騰させ、次いで1.25gの活性炭を加えた。次いで、反応混合物を濾過し、濾液を25℃の温度に冷却し、この温度に4時間維持した。次いで反応混合物をメタノールで洗い、25〜30℃の濃度で乾燥した。結果として、16.5g(収率67%)で〔1−ヒドロキシ−2−(3−ピリジニル)エチリデン〕ビスホスホン酸の半−5水和物モノナトトリウム塩を得た。
13PNMR(D2O)δ=17.8
Claims (4)
- 3−ピリジニル酢酸塩酸塩を3塩化リンと反応させて〔1−ヒドロキシ−2−(3−ピリジニル)エチリデン〕ビスホスホン酸及びその半−5水和物モノナトリウム塩を製造するに際し、3−ピリジニル酢酸塩酸塩の水溶液を0〜5℃で3塩化リンに滴加して反応させ、過剰の3塩化リンを除去し、水を加えて反応生成物を加水分解し、水に懸濁している結晶質〔1−ヒドロキシ−2−(3−ピリジニル)エチリデン〕ビスホスホン酸を単離し、ソーダ灰を加えそして得られた混合物を乾燥して
式(2):
- 3−ピリジニル酢酸塩酸塩対3塩化リン対水のモル比が1:6:7.4である請求項1の方法。
- 該塩を生ずる反応がpH4.9〜5.0で行われる請求項1の方法。
- 該塩の乾燥が25〜30℃の温度で行われる請求項1の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PL371958A PL199215B1 (pl) | 2004-12-28 | 2004-12-28 | Sposób wytwarzania kwasu [1-hydroksy-2-(3-pirydylo)etylidenobisfosfonowego] oraz jego soli monosodowej dwu i pół wodnej |
PLP.371958 | 2004-12-28 | ||
PCT/PL2005/000085 WO2006071128A1 (en) | 2004-12-28 | 2005-12-28 | Process for the preparation of [1-hydroxy-2-(3-pyridinyl)ethyliden] bisphosphonic acid and hemi-pentahydrate monosodium salt thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2008525432A true JP2008525432A (ja) | 2008-07-17 |
JP5015006B2 JP5015006B2 (ja) | 2012-08-29 |
Family
ID=35976399
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007548122A Active JP5015006B2 (ja) | 2004-12-28 | 2005-12-28 | 〔1−ヒドロキシ−2−(3−ピリジニル)エチリデン〕ビスホスホン酸及びその2.5水和物モノナトリウム塩の製造方法 |
Country Status (11)
Country | Link |
---|---|
US (1) | US8450488B2 (ja) |
EP (1) | EP1836210B1 (ja) |
JP (1) | JP5015006B2 (ja) |
KR (1) | KR100901183B1 (ja) |
AT (1) | ATE413409T1 (ja) |
DE (1) | DE602005010908D1 (ja) |
ES (1) | ES2315937T3 (ja) |
HR (1) | HRP20080619T3 (ja) |
PL (1) | PL199215B1 (ja) |
SI (1) | SI1836210T1 (ja) |
WO (1) | WO2006071128A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107011380A (zh) * | 2016-01-28 | 2017-08-04 | 臧伟 | 一种二膦酸衍生物及含二膦酸衍生物的组合物治疗骨折的应用 |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007083240A2 (en) | 2006-01-20 | 2007-07-26 | Aurobindo Pharma Limited | An improved process for the preparation of bisphosphonic acids |
US8076483B2 (en) | 2006-05-11 | 2011-12-13 | M/S. Ind Swift Laboratories Limited | Process for the preparation of pure risedronic acid or salts |
AU2007270897A1 (en) * | 2006-07-03 | 2008-01-10 | Generics [Uk] Limited | Novel process for the preparation of bisphosphonic acids |
WO2008044245A2 (en) * | 2006-10-10 | 2008-04-17 | Matrix Laboratories Ltd | A process for the preparation of risedronate sodium hemipentahydrate |
KR100775440B1 (ko) * | 2006-12-20 | 2007-11-12 | 동우신테크 주식회사 | 리세드로네이트 나트륨 헤미펜타히드레이트의 제조방법 |
KR100798855B1 (ko) | 2007-02-14 | 2008-01-28 | 주식회사 엔지켐 | 리세드론산 나트륨 헤미펜타하이드레이트의 제조방법 |
WO2009050731A2 (en) * | 2007-06-20 | 2009-04-23 | Alkem Laboratories Ltd | Novel process for preparing risedronic acid |
PL213599B1 (pl) * | 2008-10-31 | 2013-03-29 | Politechnika Gdanska | Sposób otrzymywania kwasu [1-hydroksy-2-(1H-imidazol-1-ilo)-etylideno] bisfosfonowego |
EA201270328A1 (ru) * | 2009-08-28 | 2012-09-28 | Синтон Б. В. | Способ получения 1-гидроксиалкилиден-1,1-дифосфоновых кислот |
HU230718B1 (hu) * | 2011-02-08 | 2017-11-28 | Richter Gedeon Nyrt. | Új eljárás dronsavak gyógyszeripari előállítására |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SU1719405A1 (ru) * | 1985-07-02 | 1992-03-15 | Институт Химической Кинетики И Горения Со Ан Ссср | Способ получени высших 1-оксиалкилиден-1,1-дифосфоновых кислот или их смесей, или солей |
JP2000281690A (ja) * | 1999-03-30 | 2000-10-10 | Yokkaichi Chem Co Ltd | エタン−1−ヒドロキシ−1,1−ジホスホン酸の製造方法 |
JP2002531592A (ja) * | 1998-12-01 | 2002-09-24 | バイエル アクチェンゲゼルシャフト | ホスホネート含有混合物 |
WO2003093282A1 (en) * | 2002-04-29 | 2003-11-13 | Chemi S.P.A. | Preparation of biphosphonic acids and salts thereof |
WO2003097655A1 (en) * | 2002-05-17 | 2003-11-27 | Teva Pharmaceutical Industries Ltd. | Use of certain diluents for making bisphosphonic acids |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2684286A (en) * | 1951-11-26 | 1954-07-20 | Joseph L Krieger | Preparation of phosphorous acid |
DE3016289A1 (de) * | 1980-04-28 | 1981-10-29 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung von omega -amino-1-hydroxyalkyliden-1,1-bis-phosphonsaeuren |
IL77243A (en) | 1984-12-21 | 1996-11-14 | Procter & Gamble | Pharmaceutical compositions containing geminal diphosphonic acid compounds and certain such novel compounds |
PE20011061A1 (es) * | 2000-02-01 | 2001-11-20 | Procter & Gamble | Cristalizacion selectiva del acido 3-piridil-1-hidroxi-etiliden-1,1-bisfosfonico sodio como el hemipentahidrato o el monohidrato |
US6562974B2 (en) * | 2000-02-01 | 2003-05-13 | The Procter & Gamble Company | Process for making geminal bisphosphonates |
DE10107990A1 (de) | 2001-02-19 | 2002-08-29 | Weinmann G Geraete Med | Verfahren und Vorrichtung zur Schalldämmung bei Beatmungsgeräten |
PL194770B1 (pl) * | 2001-03-19 | 2007-07-31 | Adamed Sp Z Oo | Sposób wytwarzania kwasu rizedronowego |
PL372964A1 (en) * | 2002-04-11 | 2005-08-08 | Teva Pharmaceutical Indudstries, Ltd. | Novel polymorphs and pseudopolymorphs of risedronate sodium |
ATE508134T1 (de) * | 2003-12-23 | 2011-05-15 | Alchymars S P A | Amorphe form das natriumsalzes der ibandronsäure |
-
2004
- 2004-12-28 PL PL371958A patent/PL199215B1/pl unknown
-
2005
- 2005-12-28 DE DE602005010908T patent/DE602005010908D1/de active Active
- 2005-12-28 AT AT05820284T patent/ATE413409T1/de not_active IP Right Cessation
- 2005-12-28 KR KR1020077014055A patent/KR100901183B1/ko active IP Right Grant
- 2005-12-28 EP EP05820284A patent/EP1836210B1/en active Active
- 2005-12-28 ES ES05820284T patent/ES2315937T3/es active Active
- 2005-12-28 WO PCT/PL2005/000085 patent/WO2006071128A1/en active Application Filing
- 2005-12-28 JP JP2007548122A patent/JP5015006B2/ja active Active
- 2005-12-28 SI SI200530484T patent/SI1836210T1/sl unknown
- 2005-12-28 US US11/721,334 patent/US8450488B2/en not_active Expired - Fee Related
-
2008
- 2008-11-26 HR HR20080619T patent/HRP20080619T3/xx unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SU1719405A1 (ru) * | 1985-07-02 | 1992-03-15 | Институт Химической Кинетики И Горения Со Ан Ссср | Способ получени высших 1-оксиалкилиден-1,1-дифосфоновых кислот или их смесей, или солей |
JP2002531592A (ja) * | 1998-12-01 | 2002-09-24 | バイエル アクチェンゲゼルシャフト | ホスホネート含有混合物 |
JP2000281690A (ja) * | 1999-03-30 | 2000-10-10 | Yokkaichi Chem Co Ltd | エタン−1−ヒドロキシ−1,1−ジホスホン酸の製造方法 |
WO2003093282A1 (en) * | 2002-04-29 | 2003-11-13 | Chemi S.P.A. | Preparation of biphosphonic acids and salts thereof |
WO2003097655A1 (en) * | 2002-05-17 | 2003-11-27 | Teva Pharmaceutical Industries Ltd. | Use of certain diluents for making bisphosphonic acids |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107011380A (zh) * | 2016-01-28 | 2017-08-04 | 臧伟 | 一种二膦酸衍生物及含二膦酸衍生物的组合物治疗骨折的应用 |
Also Published As
Publication number | Publication date |
---|---|
WO2006071128A1 (en) | 2006-07-06 |
HRP20080619T3 (en) | 2009-01-31 |
SI1836210T1 (sl) | 2009-02-28 |
DE602005010908D1 (de) | 2008-12-18 |
JP5015006B2 (ja) | 2012-08-29 |
ATE413409T1 (de) | 2008-11-15 |
US20090281320A1 (en) | 2009-11-12 |
PL199215B1 (pl) | 2008-08-29 |
ES2315937T3 (es) | 2009-04-01 |
EP1836210A1 (en) | 2007-09-26 |
US8450488B2 (en) | 2013-05-28 |
PL371958A1 (pl) | 2006-07-10 |
KR100901183B1 (ko) | 2009-06-04 |
KR20070086490A (ko) | 2007-08-27 |
EP1836210B1 (en) | 2008-11-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5015006B2 (ja) | 〔1−ヒドロキシ−2−(3−ピリジニル)エチリデン〕ビスホスホン酸及びその2.5水和物モノナトリウム塩の製造方法 | |
JP4642762B2 (ja) | ビスホスホン酸化合物の製造方法 | |
JP4560548B2 (ja) | イバンドロナートの製造法 | |
AU2010302597A1 (en) | Method for the manufacture of aminohydroxy diphosphonic acids | |
CZ290556B6 (cs) | Způsob čiątění kyseliny ethylendiamintetra(methylenfosfonové) nebo kyseliny 1,4,7,10-tetraazacyklododekan-1,4,7,10-tetra(methylenfosfonové) | |
RU2425049C2 (ru) | Способ получения бифосфоновых кислот и их солей | |
US8076483B2 (en) | Process for the preparation of pure risedronic acid or salts | |
JP5220843B2 (ja) | イバンドロナートのマルチステップ合成 | |
US7485726B2 (en) | Process for the preparation of risedronate sodium hemi-pentahydrate | |
EP1803727B1 (en) | Improved process for manufacture of 4-amino-hydroxybutylidene-1,1-bisphosphonic acid and its salts | |
WO2007068678A1 (en) | Process for the preparation of 3-pyridyl-1-hydroxyethylidene-1,1-biphosphonic acid and hydrated forms thereof | |
JP3901321B2 (ja) | リボフラビン−5’−リン酸またはそのナトリウム塩の製造法 | |
PL213599B1 (pl) | Sposób otrzymywania kwasu [1-hydroksy-2-(1H-imidazol-1-ilo)-etylideno] bisfosfonowego | |
US20100317859A1 (en) | Process for the Preparation of Risedronate Sodium | |
WO2007010556A1 (en) | Process for the production of 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid or salts thereof | |
KR101195631B1 (ko) | 9-[2-(포스포노메톡시)에틸]아데닌의 개선된 제조방법 | |
WO2009034580A1 (en) | Improved process for the preparation of risedronate sodium hemipentahydrate | |
JPH11269184A (ja) | ヘテロ環ビス(フォスフォン酸)誘導体の新規製造法 | |
WO2008065542A2 (en) | An improved process for the preparation of risedronate sodium | |
WO2008044245A2 (en) | A process for the preparation of risedronate sodium hemipentahydrate |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20081216 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20111220 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120319 |
|
RD03 | Notification of appointment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7423 Effective date: 20120319 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20120321 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20120508 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120606 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150615 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5015006 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |